Facile conversion of 2-azetidinones to 2-piperidones: Application to a formal synthesis of Prosopis and Cassia alkaloids

Tetrahedron

Volumn 59, Issue 34, 2003, Pages 6445-6454

  Lee, Hyeon Kyu ^a   Chun, Jong Soo ^a   Pak, Chwang Siek ^a  

^a Korea Research Institute of Chemical Technology   (South Korea)

Author keywords

2 azetidinone; 2 piperidone; Piperidine alkaloid; Ring homologation

Indexed keywords

1 (TERT BUTYLOXYCARBONYL) 3 BENZYLOXY 4 (TERT BUTYLDIPHENYLSILYLOXYMETHYL) 2 AZETIDINONE; 1 (TERT BUTYLOXYCARBONYL) 4 METHYL 3 (BENZYLOXY) 2 AZETIDINONE; 1 BENZYL 5 (BENZYLOXY) 6 (BENZYLOXYMETHYL)HEXAHYDRO 2 PYRIDINONE; 1 BENZYL 5 (BENZYLOXY) 6 METHYLHEXAHYDRO 2 PYRIDINONE; ALKALOID DERIVATIVE; AZETIDINONE DERIVATIVE; CARBON; CASSIA EXTRACT; ESTER DERIVATIVE; LACTAM DERIVATIVE; PIPERIDONE DERIVATIVE; PLANT EXTRACT; PROSOPIS EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COLUMN CHROMATOGRAPHY; DRUG SYNTHESIS; NONHUMAN; PRIORITY JOURNAL; PROSOPIS; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; SENNA; STEREOCHEMISTRY;

CASSIA; PROSOPIS;

EID: 0041743187     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)01063-9     Document Type: Article

References (93)

1. For piperidine alkaloids, see: (a) Asano N., Nash R.J., Molyneux R.J., Fleet G.W.J. Tetrahedron: Asymmetry. 11:2000;1645 (b) Michael J.P. Nat. Prod. Rep. 16:1999;675 (c) Bailey P.D., Millwood P.A., Smith P.D. Chem. Commun. 1998;633 (d) O'Hagen D. Nat. Prod. Rep. 14:1997;637 (e) Schneider M.J. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 10:1996;155-299 Pergamon, Oxford, (f) Elbein A.D., Molyneux R. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 5:1987;Wiley, New York, (g) Fodor G.B., Colasanti B. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 3:1985;1-90 Wiley, New York.
2. For piperidine alkaloids, see: (a) Asano N., Nash R.J., Molyneux R.J., Fleet G.W.J. Tetrahedron: Asymmetry. 11:2000;1645 (b) Michael J.P. Nat. Prod. Rep. 16:1999;675 (c) Bailey P.D., Millwood P.A., Smith P.D. Chem. Commun. 1998;633 (d) O'Hagen D. Nat. Prod. Rep. 14:1997;637 (e) Schneider M.J. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 10:1996;155-299 Pergamon, Oxford, (f) Elbein A.D., Molyneux R. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 5:1987;Wiley, New York, (g) Fodor G.B., Colasanti B. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 3:1985;1-90 Wiley, New York.
3. For piperidine alkaloids, see: (a) Asano N., Nash R.J., Molyneux R.J., Fleet G.W.J. Tetrahedron: Asymmetry. 11:2000;1645 (b) Michael J.P. Nat. Prod. Rep. 16:1999;675 (c) Bailey P.D., Millwood P.A., Smith P.D. Chem. Commun. 1998;633 (d) O'Hagen D. Nat. Prod. Rep. 14:1997;637 (e) Schneider M.J. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 10:1996;155-299 Pergamon, Oxford, (f) Elbein A.D., Molyneux R. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 5:1987;Wiley, New York, (g) Fodor G.B., Colasanti B. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 3:1985;1-90 Wiley, New York.
4. For piperidine alkaloids, see: (a) Asano N., Nash R.J., Molyneux R.J., Fleet G.W.J. Tetrahedron: Asymmetry. 11:2000;1645 (b) Michael J.P. Nat. Prod. Rep. 16:1999;675 (c) Bailey P.D., Millwood P.A., Smith P.D. Chem. Commun. 1998;633 (d) O'Hagen D. Nat. Prod. Rep. 14:1997;637 (e) Schneider M.J. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 10:1996;155-299 Pergamon, Oxford, (f) Elbein A.D., Molyneux R. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 5:1987;Wiley, New York, (g) Fodor G.B., Colasanti B. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 3:1985;1-90 Wiley, New York.
5. For piperidine alkaloids, see: (a) Asano N., Nash R.J., Molyneux R.J., Fleet G.W.J. Tetrahedron: Asymmetry. 11:2000;1645 (b) Michael J.P. Nat. Prod. Rep. 16:1999;675 (c) Bailey P.D., Millwood P.A., Smith P.D. Chem. Commun. 1998;633 (d) O'Hagen D. Nat. Prod. Rep. 14:1997;637 (e) Schneider M.J. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 10:1996;155-299 Pergamon, Oxford, (f) Elbein A.D., Molyneux R. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 5:1987;Wiley, New York, (g) Fodor G.B., Colasanti B. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 3:1985;1-90 Wiley, New York.
6. For piperidine alkaloids, see: (a) Asano N., Nash R.J., Molyneux R.J., Fleet G.W.J. Tetrahedron: Asymmetry. 11:2000;1645 (b) Michael J.P. Nat. Prod. Rep. 16:1999;675 (c) Bailey P.D., Millwood P.A., Smith P.D. Chem. Commun. 1998;633 (d) O'Hagen D. Nat. Prod. Rep. 14:1997;637 (e) Schneider M.J. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 10:1996;155-299 Pergamon, Oxford, (f) Elbein A.D., Molyneux R. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 5:1987;Wiley, New York, (g) Fodor G.B., Colasanti B. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 3:1985;1-90 Wiley, New York.
7. For piperidine alkaloids, see: (a) Asano N., Nash R.J., Molyneux R.J., Fleet G.W.J. Tetrahedron: Asymmetry. 11:2000;1645 (b) Michael J.P. Nat. Prod. Rep. 16:1999;675 (c) Bailey P.D., Millwood P.A., Smith P.D. Chem. Commun. 1998;633 (d) O'Hagen D. Nat. Prod. Rep. 14:1997;637 (e) Schneider M.J. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 10:1996;155-299 Pergamon, Oxford, (f) Elbein A.D., Molyneux R. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 5:1987;Wiley, New York, (g) Fodor G.B., Colasanti B. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 3:1985;1-90 Wiley, New York.
8. For Prosopis & Cassia alkaloids, see: (a) Astudillo S.L., Jurgens S.K., SchmedaHirschmann G., Griffith G.A., Holt D.H., Jenkins P.R. Planta Med. 65:1999;161 (b) Bolzani V., da S., Gunatilaka A.A.L., Kingston D.G.I. Tetrahedron. 51:1995;5929 (c) Aguinaldo A.M., Read R.W. Phytochemistry. 29:1990;2309 (d) Strunz G.M., Findlay J.A. Brossi A. The Alkaloids. Vol. 26:1985;89-183 Academic, New York, (e) Khuong-Huu Q., Ratle G., Monseur X., Goutrarel R. Bull. Soc. Chim. Belg. 81:1972;425 (f) Ratle G., Monseur X., Das B., Yassi J., Khuong-Huu Q., Goutrarel R. Bull. Soc. Chim. Fr. 1966;2945.
9. For Prosopis & Cassia alkaloids, see: (a) Astudillo S.L., Jurgens S.K., SchmedaHirschmann G., Griffith G.A., Holt D.H., Jenkins P.R. Planta Med. 65:1999;161 (b) Bolzani V., da S., Gunatilaka A.A.L., Kingston D.G.I. Tetrahedron. 51:1995;5929 (c) Aguinaldo A.M., Read R.W. Phytochemistry. 29:1990;2309 (d) Strunz G.M., Findlay J.A. Brossi A. The Alkaloids. Vol. 26:1985;89-183 Academic, New York, (e) Khuong-Huu Q., Ratle G., Monseur X., Goutrarel R. Bull. Soc. Chim. Belg. 81:1972;425 (f) Ratle G., Monseur X., Das B., Yassi J., Khuong-Huu Q., Goutrarel R. Bull. Soc. Chim. Fr. 1966;2945.
10. For Prosopis & Cassia alkaloids, see: (a) Astudillo S.L., Jurgens S.K., SchmedaHirschmann G., Griffith G.A., Holt D.H., Jenkins P.R. Planta Med. 65:1999;161 (b) Bolzani V., da S., Gunatilaka A.A.L., Kingston D.G.I. Tetrahedron. 51:1995;5929 (c) Aguinaldo A.M., Read R.W. Phytochemistry. 29:1990;2309 (d) Strunz G.M., Findlay J.A. Brossi A. The Alkaloids. Vol. 26:1985;89-183 Academic, New York, (e) Khuong-Huu Q., Ratle G., Monseur X., Goutrarel R. Bull. Soc. Chim. Belg. 81:1972;425 (f) Ratle G., Monseur X., Das B., Yassi J., Khuong-Huu Q., Goutrarel R. Bull. Soc. Chim. Fr. 1966;2945.
11. For Prosopis & Cassia alkaloids, see: (a) Astudillo S.L., Jurgens S.K., SchmedaHirschmann G., Griffith G.A., Holt D.H., Jenkins P.R. Planta Med. 65:1999;161 (b) Bolzani V., da S., Gunatilaka A.A.L., Kingston D.G.I. Tetrahedron. 51:1995;5929 (c) Aguinaldo A.M., Read R.W. Phytochemistry. 29:1990;2309 (d) Strunz G.M., Findlay J.A. Brossi A. The Alkaloids. Vol. 26:1985;89-183 Academic, New York, (e) Khuong-Huu Q., Ratle G., Monseur X., Goutrarel R. Bull. Soc. Chim. Belg. 81:1972;425 (f) Ratle G., Monseur X., Das B., Yassi J., Khuong-Huu Q., Goutrarel R. Bull. Soc. Chim. Fr. 1966;2945.
12. For Prosopis & Cassia alkaloids, see: (a) Astudillo S.L., Jurgens S.K., SchmedaHirschmann G., Griffith G.A., Holt D.H., Jenkins P.R. Planta Med. 65:1999;161 (b) Bolzani V., da S., Gunatilaka A.A.L., Kingston D.G.I. Tetrahedron. 51:1995;5929 (c) Aguinaldo A.M., Read R.W. Phytochemistry. 29:1990;2309 (d) Strunz G.M., Findlay J.A. Brossi A. The Alkaloids. Vol. 26:1985;89-183 Academic, New York, (e) Khuong-Huu Q., Ratle G., Monseur X., Goutrarel R. Bull. Soc. Chim. Belg. 81:1972;425 (f) Ratle G., Monseur X., Das B., Yassi J., Khuong-Huu Q., Goutrarel R. Bull. Soc. Chim. Fr. 1966;2945.
13. For Prosopis & Cassia alkaloids, see: (a) Astudillo S.L., Jurgens S.K., SchmedaHirschmann G., Griffith G.A., Holt D.H., Jenkins P.R. Planta Med. 65:1999;161 (b) Bolzani V., da S., Gunatilaka A.A.L., Kingston D.G.I. Tetrahedron. 51:1995;5929 (c) Aguinaldo A.M., Read R.W. Phytochemistry. 29:1990;2309 (d) Strunz G.M., Findlay J.A. Brossi A. The Alkaloids. Vol. 26:1985;89-183 Academic, New York, (e) Khuong-Huu Q., Ratle G., Monseur X., Goutrarel R. Bull. Soc. Chim. Belg. 81:1972;425 (f) Ratle G., Monseur X., Das B., Yassi J., Khuong-Huu Q., Goutrarel R. Bull. Soc. Chim. Fr. 1966;2945.
14. For some recent example of synthesis of piperidine alkaloids, see: (a) Johnson T.A., Curtis M.D., Beak P. J. Am. Chem. Soc. 123:2001;1004 (b) Nishimura Y., Adachi H., Satoh T., Shitara E., Nakamura H., Kojima F., Takeuchi T. J. Org. Chem. 65:2000;4871 (c) Amat M., Bosch J., Hidalgo J., Canto M., Perez M., Llor N., Molins E., Miravitlles C., Orozco M., Luque J. J. Org. Chem. 65:2000;3074 (d) Sun H., Millar K.M., Yang J., Abboud K., Horenstein B.A. Tetrahedron Lett. 41:2000;2801 (e) Yokoyama H., Otaya K., Kobayashi H., Miyazawa M., Yamaguchi S., Hirai Y. Org. Lett. 2:2000;2427 (f) Williams S.J., Hoos R., Winters S.G. J. Am. Chem. Soc. 122:2000;2223 (g) Laschat S., Dickner T. Synthesis. 2000;1781 (h) Davis F.A., Chao B., Fang T., Szewczyk J.M. Org. Lett. 2:2000;1041 (i) Comins D.L., Kuethe J.T., Hong H., Lakner F.J., Concolino T.E., Rheingold A.L. J. Am. Chem. Soc. 121:1999;2651 (j) Kiguchi T., Shirakawa M., Honda R., Ninomiya I., Naito T. Tetrahedron. 54:1998;15589 (k) Pahl A., Wartchow R., Meyer H.H. Tetrahedron Lett. 39:1998;2095 (l) Bailey P.D., Millwood P.A., Smith P.D. J. Chem. Soc. Chem. Commun. 1998;633 (m) Bayquen A.V., Read R.W. Tetrahedron. 52:1996;13467 (n) Altenbach H.-J., Himmeldirk K. Tetrahedron: Asymmetry. 6:1995;1077 (o) Nukui S., Sodeoka M., Sasai H., Shibasaki M. J. Org. Chem. 60:1995;398 (p) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575.
15. For some recent example of synthesis of piperidine alkaloids, see: (a) Johnson T.A., Curtis M.D., Beak P. J. Am. Chem. Soc. 123:2001;1004 (b) Nishimura Y., Adachi H., Satoh T., Shitara E., Nakamura H., Kojima F., Takeuchi T. J. Org. Chem. 65:2000;4871 (c) Amat M., Bosch J., Hidalgo J., Canto M., Perez M., Llor N., Molins E., Miravitlles C., Orozco M., Luque J. J. Org. Chem. 65:2000;3074 (d) Sun H., Millar K.M., Yang J., Abboud K., Horenstein B.A. Tetrahedron Lett. 41:2000;2801 (e) Yokoyama H., Otaya K., Kobayashi H., Miyazawa M., Yamaguchi S., Hirai Y. Org. Lett. 2:2000;2427 (f) Williams S.J., Hoos R., Winters S.G. J. Am. Chem. Soc. 122:2000;2223 (g) Laschat S., Dickner T. Synthesis. 2000;1781 (h) Davis F.A., Chao B., Fang T., Szewczyk J.M. Org. Lett. 2:2000;1041 (i) Comins D.L., Kuethe J.T., Hong H., Lakner F.J., Concolino T.E., Rheingold A.L. J. Am. Chem. Soc. 121:1999;2651 (j) Kiguchi T., Shirakawa M., Honda R., Ninomiya I., Naito T. Tetrahedron. 54:1998;15589 (k) Pahl A., Wartchow R., Meyer H.H. Tetrahedron Lett. 39:1998;2095 (l) Bailey P.D., Millwood P.A., Smith P.D. J. Chem. Soc. Chem. Commun. 1998;633 (m) Bayquen A.V., Read R.W. Tetrahedron. 52:1996;13467 (n) Altenbach H.-J., Himmeldirk K. Tetrahedron: Asymmetry. 6:1995;1077 (o) Nukui S., Sodeoka M., Sasai H., Shibasaki M. J. Org. Chem. 60:1995;398 (p) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575.
16. For some recent example of synthesis of piperidine alkaloids, see: (a) Johnson T.A., Curtis M.D., Beak P. J. Am. Chem. Soc. 123:2001;1004 (b) Nishimura Y., Adachi H., Satoh T., Shitara E., Nakamura H., Kojima F., Takeuchi T. J. Org. Chem. 65:2000;4871 (c) Amat M., Bosch J., Hidalgo J., Canto M., Perez M., Llor N., Molins E., Miravitlles C., Orozco M., Luque J. J. Org. Chem. 65:2000;3074 (d) Sun H., Millar K.M., Yang J., Abboud K., Horenstein B.A. Tetrahedron Lett. 41:2000;2801 (e) Yokoyama H., Otaya K., Kobayashi H., Miyazawa M., Yamaguchi S., Hirai Y. Org. Lett. 2:2000;2427 (f) Williams S.J., Hoos R., Winters S.G. J. Am. Chem. Soc. 122:2000;2223 (g) Laschat S., Dickner T. Synthesis. 2000;1781 (h) Davis F.A., Chao B., Fang T., Szewczyk J.M. Org. Lett. 2:2000;1041 (i) Comins D.L., Kuethe J.T., Hong H., Lakner F.J., Concolino T.E., Rheingold A.L. J. Am. Chem. Soc. 121:1999;2651 (j) Kiguchi T., Shirakawa M., Honda R., Ninomiya I., Naito T. Tetrahedron. 54:1998;15589 (k) Pahl A., Wartchow R., Meyer H.H. Tetrahedron Lett. 39:1998;2095 (l) Bailey P.D., Millwood P.A., Smith P.D. J. Chem. Soc. Chem. Commun. 1998;633 (m) Bayquen A.V., Read R.W. Tetrahedron. 52:1996;13467 (n) Altenbach H.-J., Himmeldirk K. Tetrahedron: Asymmetry. 6:1995;1077 (o) Nukui S., Sodeoka M., Sasai H., Shibasaki M. J. Org. Chem. 60:1995;398 (p) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575.
17. For some recent example of synthesis of piperidine alkaloids, see: (a) Johnson T.A., Curtis M.D., Beak P. J. Am. Chem. Soc. 123:2001;1004 (b) Nishimura Y., Adachi H., Satoh T., Shitara E., Nakamura H., Kojima F., Takeuchi T. J. Org. Chem. 65:2000;4871 (c) Amat M., Bosch J., Hidalgo J., Canto M., Perez M., Llor N., Molins E., Miravitlles C., Orozco M., Luque J. J. Org. Chem. 65:2000;3074 (d) Sun H., Millar K.M., Yang J., Abboud K., Horenstein B.A. Tetrahedron Lett. 41:2000;2801 (e) Yokoyama H., Otaya K., Kobayashi H., Miyazawa M., Yamaguchi S., Hirai Y. Org. Lett. 2:2000;2427 (f) Williams S.J., Hoos R., Winters S.G. J. Am. Chem. Soc. 122:2000;2223 (g) Laschat S., Dickner T. Synthesis. 2000;1781 (h) Davis F.A., Chao B., Fang T., Szewczyk J.M. Org. Lett. 2:2000;1041 (i) Comins D.L., Kuethe J.T., Hong H., Lakner F.J., Concolino T.E., Rheingold A.L. J. Am. Chem. Soc. 121:1999;2651 (j) Kiguchi T., Shirakawa M., Honda R., Ninomiya I., Naito T. Tetrahedron. 54:1998;15589 (k) Pahl A., Wartchow R., Meyer H.H. Tetrahedron Lett. 39:1998;2095 (l) Bailey P.D., Millwood P.A., Smith P.D. J. Chem. Soc. Chem. Commun. 1998;633 (m) Bayquen A.V., Read R.W. Tetrahedron. 52:1996;13467 (n) Altenbach H.-J., Himmeldirk K. Tetrahedron: Asymmetry. 6:1995;1077 (o) Nukui S., Sodeoka M., Sasai H., Shibasaki M. J. Org. Chem. 60:1995;398 (p) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575.
18. For some recent example of synthesis of piperidine alkaloids, see: (a) Johnson T.A., Curtis M.D., Beak P. J. Am. Chem. Soc. 123:2001;1004 (b) Nishimura Y., Adachi H., Satoh T., Shitara E., Nakamura H., Kojima F., Takeuchi T. J. Org. Chem. 65:2000;4871 (c) Amat M., Bosch J., Hidalgo J., Canto M., Perez M., Llor N., Molins E., Miravitlles C., Orozco M., Luque J. J. Org. Chem. 65:2000;3074 (d) Sun H., Millar K.M., Yang J., Abboud K., Horenstein B.A. Tetrahedron Lett. 41:2000;2801 (e) Yokoyama H., Otaya K., Kobayashi H., Miyazawa M., Yamaguchi S., Hirai Y. Org. Lett. 2:2000;2427 (f) Williams S.J., Hoos R., Winters S.G. J. Am. Chem. Soc. 122:2000;2223 (g) Laschat S., Dickner T. Synthesis. 2000;1781 (h) Davis F.A., Chao B., Fang T., Szewczyk J.M. Org. Lett. 2:2000;1041 (i) Comins D.L., Kuethe J.T., Hong H., Lakner F.J., Concolino T.E., Rheingold A.L. J. Am. Chem. Soc. 121:1999;2651 (j) Kiguchi T., Shirakawa M., Honda R., Ninomiya I., Naito T. Tetrahedron. 54:1998;15589 (k) Pahl A., Wartchow R., Meyer H.H. Tetrahedron Lett. 39:1998;2095 (l) Bailey P.D., Millwood P.A., Smith P.D. J. Chem. Soc. Chem. Commun. 1998;633 (m) Bayquen A.V., Read R.W. Tetrahedron. 52:1996;13467 (n) Altenbach H.-J., Himmeldirk K. Tetrahedron: Asymmetry. 6:1995;1077 (o) Nukui S., Sodeoka M., Sasai H., Shibasaki M. J. Org. Chem. 60:1995;398 (p) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575.
19. For some recent example of synthesis of piperidine alkaloids, see: (a) Johnson T.A., Curtis M.D., Beak P. J. Am. Chem. Soc. 123:2001;1004 (b) Nishimura Y., Adachi H., Satoh T., Shitara E., Nakamura H., Kojima F., Takeuchi T. J. Org. Chem. 65:2000;4871 (c) Amat M., Bosch J., Hidalgo J., Canto M., Perez M., Llor N., Molins E., Miravitlles C., Orozco M., Luque J. J. Org. Chem. 65:2000;3074 (d) Sun H., Millar K.M., Yang J., Abboud K., Horenstein B.A. Tetrahedron Lett. 41:2000;2801 (e) Yokoyama H., Otaya K., Kobayashi H., Miyazawa M., Yamaguchi S., Hirai Y. Org. Lett. 2:2000;2427 (f) Williams S.J., Hoos R., Winters S.G. J. Am. Chem. Soc. 122:2000;2223 (g) Laschat S., Dickner T. Synthesis. 2000;1781 (h) Davis F.A., Chao B., Fang T., Szewczyk J.M. Org. Lett. 2:2000;1041 (i) Comins D.L., Kuethe J.T., Hong H., Lakner F.J., Concolino T.E., Rheingold A.L. J. Am. Chem. Soc. 121:1999;2651 (j) Kiguchi T., Shirakawa M., Honda R., Ninomiya I., Naito T. Tetrahedron. 54:1998;15589 (k) Pahl A., Wartchow R., Meyer H.H. Tetrahedron Lett. 39:1998;2095 (l) Bailey P.D., Millwood P.A., Smith P.D. J. Chem. Soc. Chem. Commun. 1998;633 (m) Bayquen A.V., Read R.W. Tetrahedron. 52:1996;13467 (n) Altenbach H.-J., Himmeldirk K. Tetrahedron: Asymmetry. 6:1995;1077 (o) Nukui S., Sodeoka M., Sasai H., Shibasaki M. J. Org. Chem. 60:1995;398 (p) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575.
20. For some recent example of synthesis of piperidine alkaloids, see: (a) Johnson T.A., Curtis M.D., Beak P. J. Am. Chem. Soc. 123:2001;1004 (b) Nishimura Y., Adachi H., Satoh T., Shitara E., Nakamura H., Kojima F., Takeuchi T. J. Org. Chem. 65:2000;4871 (c) Amat M., Bosch J., Hidalgo J., Canto M., Perez M., Llor N., Molins E., Miravitlles C., Orozco M., Luque J. J. Org. Chem. 65:2000;3074 (d) Sun H., Millar K.M., Yang J., Abboud K., Horenstein B.A. Tetrahedron Lett. 41:2000;2801 (e) Yokoyama H., Otaya K., Kobayashi H., Miyazawa M., Yamaguchi S., Hirai Y. Org. Lett. 2:2000;2427 (f) Williams S.J., Hoos R., Winters S.G. J. Am. Chem. Soc. 122:2000;2223 (g) Laschat S., Dickner T. Synthesis. 2000;1781 (h) Davis F.A., Chao B., Fang T., Szewczyk J.M. Org. Lett. 2:2000;1041 (i) Comins D.L., Kuethe J.T., Hong H., Lakner F.J., Concolino T.E., Rheingold A.L. J. Am. Chem. Soc. 121:1999;2651 (j) Kiguchi T., Shirakawa M., Honda R., Ninomiya I., Naito T. Tetrahedron. 54:1998;15589 (k) Pahl A., Wartchow R., Meyer H.H. Tetrahedron Lett. 39:1998;2095 (l) Bailey P.D., Millwood P.A., Smith P.D. J. Chem. Soc. Chem. Commun. 1998;633 (m) Bayquen A.V., Read R.W. Tetrahedron. 52:1996;13467 (n) Altenbach H.-J., Himmeldirk K. Tetrahedron: Asymmetry. 6:1995;1077 (o) Nukui S., Sodeoka M., Sasai H., Shibasaki M. J. Org. Chem. 60:1995;398 (p) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575.
21. For some recent example of synthesis of piperidine alkaloids, see: (a) Johnson T.A., Curtis M.D., Beak P. J. Am. Chem. Soc. 123:2001;1004 (b) Nishimura Y., Adachi H., Satoh T., Shitara E., Nakamura H., Kojima F., Takeuchi T. J. Org. Chem. 65:2000;4871 (c) Amat M., Bosch J., Hidalgo J., Canto M., Perez M., Llor N., Molins E., Miravitlles C., Orozco M., Luque J. J. Org. Chem. 65:2000;3074 (d) Sun H., Millar K.M., Yang J., Abboud K., Horenstein B.A. Tetrahedron Lett. 41:2000;2801 (e) Yokoyama H., Otaya K., Kobayashi H., Miyazawa M., Yamaguchi S., Hirai Y. Org. Lett. 2:2000;2427 (f) Williams S.J., Hoos R., Winters S.G. J. Am. Chem. Soc. 122:2000;2223 (g) Laschat S., Dickner T. Synthesis. 2000;1781 (h) Davis F.A., Chao B., Fang T., Szewczyk J.M. Org. Lett. 2:2000;1041 (i) Comins D.L., Kuethe J.T., Hong H., Lakner F.J., Concolino T.E., Rheingold A.L. J. Am. Chem. Soc. 121:1999;2651 (j) Kiguchi T., Shirakawa M., Honda R., Ninomiya I., Naito T. Tetrahedron. 54:1998;15589 (k) Pahl A., Wartchow R., Meyer H.H. Tetrahedron Lett. 39:1998;2095 (l) Bailey P.D., Millwood P.A., Smith P.D. J. Chem. Soc. Chem. Commun. 1998;633 (m) Bayquen A.V., Read R.W. Tetrahedron. 52:1996;13467 (n) Altenbach H.-J., Himmeldirk K. Tetrahedron: Asymmetry. 6:1995;1077 (o) Nukui S., Sodeoka M., Sasai H., Shibasaki M. J. Org. Chem. 60:1995;398 (p) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575.
22. For some recent example of synthesis of piperidine alkaloids, see: (a) Johnson T.A., Curtis M.D., Beak P. J. Am. Chem. Soc. 123:2001;1004 (b) Nishimura Y., Adachi H., Satoh T., Shitara E., Nakamura H., Kojima F., Takeuchi T. J. Org. Chem. 65:2000;4871 (c) Amat M., Bosch J., Hidalgo J., Canto M., Perez M., Llor N., Molins E., Miravitlles C., Orozco M., Luque J. J. Org. Chem. 65:2000;3074 (d) Sun H., Millar K.M., Yang J., Abboud K., Horenstein B.A. Tetrahedron Lett. 41:2000;2801 (e) Yokoyama H., Otaya K., Kobayashi H., Miyazawa M., Yamaguchi S., Hirai Y. Org. Lett. 2:2000;2427 (f) Williams S.J., Hoos R., Winters S.G. J. Am. Chem. Soc. 122:2000;2223 (g) Laschat S., Dickner T. Synthesis. 2000;1781 (h) Davis F.A., Chao B., Fang T., Szewczyk J.M. Org. Lett. 2:2000;1041 (i) Comins D.L., Kuethe J.T., Hong H., Lakner F.J., Concolino T.E., Rheingold A.L. J. Am. Chem. Soc. 121:1999;2651 (j) Kiguchi T., Shirakawa M., Honda R., Ninomiya I., Naito T. Tetrahedron. 54:1998;15589 (k) Pahl A., Wartchow R., Meyer H.H. Tetrahedron Lett. 39:1998;2095 (l) Bailey P.D., Millwood P.A., Smith P.D. J. Chem. Soc. Chem. Commun. 1998;633 (m) Bayquen A.V., Read R.W. Tetrahedron. 52:1996;13467 (n) Altenbach H.-J., Himmeldirk K. Tetrahedron: Asymmetry. 6:1995;1077 (o) Nukui S., Sodeoka M., Sasai H., Shibasaki M. J. Org. Chem. 60:1995;398 (p) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575.
23. For some recent example of synthesis of piperidine alkaloids, see: (a) Johnson T.A., Curtis M.D., Beak P. J. Am. Chem. Soc. 123:2001;1004 (b) Nishimura Y., Adachi H., Satoh T., Shitara E., Nakamura H., Kojima F., Takeuchi T. J. Org. Chem. 65:2000;4871 (c) Amat M., Bosch J., Hidalgo J., Canto M., Perez M., Llor N., Molins E., Miravitlles C., Orozco M., Luque J. J. Org. Chem. 65:2000;3074 (d) Sun H., Millar K.M., Yang J., Abboud K., Horenstein B.A. Tetrahedron Lett. 41:2000;2801 (e) Yokoyama H., Otaya K., Kobayashi H., Miyazawa M., Yamaguchi S., Hirai Y. Org. Lett. 2:2000;2427 (f) Williams S.J., Hoos R., Winters S.G. J. Am. Chem. Soc. 122:2000;2223 (g) Laschat S., Dickner T. Synthesis. 2000;1781 (h) Davis F.A., Chao B., Fang T., Szewczyk J.M. Org. Lett. 2:2000;1041 (i) Comins D.L., Kuethe J.T., Hong H., Lakner F.J., Concolino T.E., Rheingold A.L. J. Am. Chem. Soc. 121:1999;2651 (j) Kiguchi T., Shirakawa M., Honda R., Ninomiya I., Naito T. Tetrahedron. 54:1998;15589 (k) Pahl A., Wartchow R., Meyer H.H. Tetrahedron Lett. 39:1998;2095 (l) Bailey P.D., Millwood P.A., Smith P.D. J. Chem. Soc. Chem. Commun. 1998;633 (m) Bayquen A.V., Read R.W. Tetrahedron. 52:1996;13467 (n) Altenbach H.-J., Himmeldirk K. Tetrahedron: Asymmetry. 6:1995;1077 (o) Nukui S., Sodeoka M., Sasai H., Shibasaki M. J. Org. Chem. 60:1995;398 (p) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575.
24. For some recent example of synthesis of piperidine alkaloids, see: (a) Johnson T.A., Curtis M.D., Beak P. J. Am. Chem. Soc. 123:2001;1004 (b) Nishimura Y., Adachi H., Satoh T., Shitara E., Nakamura H., Kojima F., Takeuchi T. J. Org. Chem. 65:2000;4871 (c) Amat M., Bosch J., Hidalgo J., Canto M., Perez M., Llor N., Molins E., Miravitlles C., Orozco M., Luque J. J. Org. Chem. 65:2000;3074 (d) Sun H., Millar K.M., Yang J., Abboud K., Horenstein B.A. Tetrahedron Lett. 41:2000;2801 (e) Yokoyama H., Otaya K., Kobayashi H., Miyazawa M., Yamaguchi S., Hirai Y. Org. Lett. 2:2000;2427 (f) Williams S.J., Hoos R., Winters S.G. J. Am. Chem. Soc. 122:2000;2223 (g) Laschat S., Dickner T. Synthesis. 2000;1781 (h) Davis F.A., Chao B., Fang T., Szewczyk J.M. Org. Lett. 2:2000;1041 (i) Comins D.L., Kuethe J.T., Hong H., Lakner F.J., Concolino T.E., Rheingold A.L. J. Am. Chem. Soc. 121:1999;2651 (j) Kiguchi T., Shirakawa M., Honda R., Ninomiya I., Naito T. Tetrahedron. 54:1998;15589 (k) Pahl A., Wartchow R., Meyer H.H. Tetrahedron Lett. 39:1998;2095 (l) Bailey P.D., Millwood P.A., Smith P.D. J. Chem. Soc. Chem. Commun. 1998;633 (m) Bayquen A.V., Read R.W. Tetrahedron. 52:1996;13467 (n) Altenbach H.-J., Himmeldirk K. Tetrahedron: Asymmetry. 6:1995;1077 (o) Nukui S., Sodeoka M., Sasai H., Shibasaki M. J. Org. Chem. 60:1995;398 (p) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575.
25. For some recent example of synthesis of piperidine alkaloids, see: (a) Johnson T.A., Curtis M.D., Beak P. J. Am. Chem. Soc. 123:2001;1004 (b) Nishimura Y., Adachi H., Satoh T., Shitara E., Nakamura H., Kojima F., Takeuchi T. J. Org. Chem. 65:2000;4871 (c) Amat M., Bosch J., Hidalgo J., Canto M., Perez M., Llor N., Molins E., Miravitlles C., Orozco M., Luque J. J. Org. Chem. 65:2000;3074 (d) Sun H., Millar K.M., Yang J., Abboud K., Horenstein B.A. Tetrahedron Lett. 41:2000;2801 (e) Yokoyama H., Otaya K., Kobayashi H., Miyazawa M., Yamaguchi S., Hirai Y. Org. Lett. 2:2000;2427 (f) Williams S.J., Hoos R., Winters S.G. J. Am. Chem. Soc. 122:2000;2223 (g) Laschat S., Dickner T. Synthesis. 2000;1781 (h) Davis F.A., Chao B., Fang T., Szewczyk J.M. Org. Lett. 2:2000;1041 (i) Comins D.L., Kuethe J.T., Hong H., Lakner F.J., Concolino T.E., Rheingold A.L. J. Am. Chem. Soc. 121:1999;2651 (j) Kiguchi T., Shirakawa M., Honda R., Ninomiya I., Naito T. Tetrahedron. 54:1998;15589 (k) Pahl A., Wartchow R., Meyer H.H. Tetrahedron Lett. 39:1998;2095 (l) Bailey P.D., Millwood P.A., Smith P.D. J. Chem. Soc. Chem. Commun. 1998;633 (m) Bayquen A.V., Read R.W. Tetrahedron. 52:1996;13467 (n) Altenbach H.-J., Himmeldirk K. Tetrahedron: Asymmetry. 6:1995;1077 (o) Nukui S., Sodeoka M., Sasai H., Shibasaki M. J. Org. Chem. 60:1995;398 (p) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575.
26. For some recent example of synthesis of piperidine alkaloids, see: (a) Johnson T.A., Curtis M.D., Beak P. J. Am. Chem. Soc. 123:2001;1004 (b) Nishimura Y., Adachi H., Satoh T., Shitara E., Nakamura H., Kojima F., Takeuchi T. J. Org. Chem. 65:2000;4871 (c) Amat M., Bosch J., Hidalgo J., Canto M., Perez M., Llor N., Molins E., Miravitlles C., Orozco M., Luque J. J. Org. Chem. 65:2000;3074 (d) Sun H., Millar K.M., Yang J., Abboud K., Horenstein B.A. Tetrahedron Lett. 41:2000;2801 (e) Yokoyama H., Otaya K., Kobayashi H., Miyazawa M., Yamaguchi S., Hirai Y. Org. Lett. 2:2000;2427 (f) Williams S.J., Hoos R., Winters S.G. J. Am. Chem. Soc. 122:2000;2223 (g) Laschat S., Dickner T. Synthesis. 2000;1781 (h) Davis F.A., Chao B., Fang T., Szewczyk J.M. Org. Lett. 2:2000;1041 (i) Comins D.L., Kuethe J.T., Hong H., Lakner F.J., Concolino T.E., Rheingold A.L. J. Am. Chem. Soc. 121:1999;2651 (j) Kiguchi T., Shirakawa M., Honda R., Ninomiya I., Naito T. Tetrahedron. 54:1998;15589 (k) Pahl A., Wartchow R., Meyer H.H. Tetrahedron Lett. 39:1998;2095 (l) Bailey P.D., Millwood P.A., Smith P.D. J. Chem. Soc. Chem. Commun. 1998;633 (m) Bayquen A.V., Read R.W. Tetrahedron. 52:1996;13467 (n) Altenbach H.-J., Himmeldirk K. Tetrahedron: Asymmetry. 6:1995;1077 (o) Nukui S., Sodeoka M., Sasai H., Shibasaki M. J. Org. Chem. 60:1995;398 (p) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575.
27. For some recent example of synthesis of piperidine alkaloids, see: (a) Johnson T.A., Curtis M.D., Beak P. J. Am. Chem. Soc. 123:2001;1004 (b) Nishimura Y., Adachi H., Satoh T., Shitara E., Nakamura H., Kojima F., Takeuchi T. J. Org. Chem. 65:2000;4871 (c) Amat M., Bosch J., Hidalgo J., Canto M., Perez M., Llor N., Molins E., Miravitlles C., Orozco M., Luque J. J. Org. Chem. 65:2000;3074 (d) Sun H., Millar K.M., Yang J., Abboud K., Horenstein B.A. Tetrahedron Lett. 41:2000;2801 (e) Yokoyama H., Otaya K., Kobayashi H., Miyazawa M., Yamaguchi S., Hirai Y. Org. Lett. 2:2000;2427 (f) Williams S.J., Hoos R., Winters S.G. J. Am. Chem. Soc. 122:2000;2223 (g) Laschat S., Dickner T. Synthesis. 2000;1781 (h) Davis F.A., Chao B., Fang T., Szewczyk J.M. Org. Lett. 2:2000;1041 (i) Comins D.L., Kuethe J.T., Hong H., Lakner F.J., Concolino T.E., Rheingold A.L. J. Am. Chem. Soc. 121:1999;2651 (j) Kiguchi T., Shirakawa M., Honda R., Ninomiya I., Naito T. Tetrahedron. 54:1998;15589 (k) Pahl A., Wartchow R., Meyer H.H. Tetrahedron Lett. 39:1998;2095 (l) Bailey P.D., Millwood P.A., Smith P.D. J. Chem. Soc. Chem. Commun. 1998;633 (m) Bayquen A.V., Read R.W. Tetrahedron. 52:1996;13467 (n) Altenbach H.-J., Himmeldirk K. Tetrahedron: Asymmetry. 6:1995;1077 (o) Nukui S., Sodeoka M., Sasai H., Shibasaki M. J. Org. Chem. 60:1995;398 (p) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575.
28. For some recent example of synthesis of piperidine alkaloids, see: (a) Johnson T.A., Curtis M.D., Beak P. J. Am. Chem. Soc. 123:2001;1004 (b) Nishimura Y., Adachi H., Satoh T., Shitara E., Nakamura H., Kojima F., Takeuchi T. J. Org. Chem. 65:2000;4871 (c) Amat M., Bosch J., Hidalgo J., Canto M., Perez M., Llor N., Molins E., Miravitlles C., Orozco M., Luque J. J. Org. Chem. 65:2000;3074 (d) Sun H., Millar K.M., Yang J., Abboud K., Horenstein B.A. Tetrahedron Lett. 41:2000;2801 (e) Yokoyama H., Otaya K., Kobayashi H., Miyazawa M., Yamaguchi S., Hirai Y. Org. Lett. 2:2000;2427 (f) Williams S.J., Hoos R., Winters S.G. J. Am. Chem. Soc. 122:2000;2223 (g) Laschat S., Dickner T. Synthesis. 2000;1781 (h) Davis F.A., Chao B., Fang T., Szewczyk J.M. Org. Lett. 2:2000;1041 (i) Comins D.L., Kuethe J.T., Hong H., Lakner F.J., Concolino T.E., Rheingold A.L. J. Am. Chem. Soc. 121:1999;2651 (j) Kiguchi T., Shirakawa M., Honda R., Ninomiya I., Naito T. Tetrahedron. 54:1998;15589 (k) Pahl A., Wartchow R., Meyer H.H. Tetrahedron Lett. 39:1998;2095 (l) Bailey P.D., Millwood P.A., Smith P.D. J. Chem. Soc. Chem. Commun. 1998;633 (m) Bayquen A.V., Read R.W. Tetrahedron. 52:1996;13467 (n) Altenbach H.-J., Himmeldirk K. Tetrahedron: Asymmetry. 6:1995;1077 (o) Nukui S., Sodeoka M., Sasai H., Shibasaki M. J. Org. Chem. 60:1995;398 (p) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575.
29. For some recent example of synthesis of piperidine alkaloids, see: (a) Johnson T.A., Curtis M.D., Beak P. J. Am. Chem. Soc. 123:2001;1004 (b) Nishimura Y., Adachi H., Satoh T., Shitara E., Nakamura H., Kojima F., Takeuchi T. J. Org. Chem. 65:2000;4871 (c) Amat M., Bosch J., Hidalgo J., Canto M., Perez M., Llor N., Molins E., Miravitlles C., Orozco M., Luque J. J. Org. Chem. 65:2000;3074 (d) Sun H., Millar K.M., Yang J., Abboud K., Horenstein B.A. Tetrahedron Lett. 41:2000;2801 (e) Yokoyama H., Otaya K., Kobayashi H., Miyazawa M., Yamaguchi S., Hirai Y. Org. Lett. 2:2000;2427 (f) Williams S.J., Hoos R., Winters S.G. J. Am. Chem. Soc. 122:2000;2223 (g) Laschat S., Dickner T. Synthesis. 2000;1781 (h) Davis F.A., Chao B., Fang T., Szewczyk J.M. Org. Lett. 2:2000;1041 (i) Comins D.L., Kuethe J.T., Hong H., Lakner F.J., Concolino T.E., Rheingold A.L. J. Am. Chem. Soc. 121:1999;2651 (j) Kiguchi T., Shirakawa M., Honda R., Ninomiya I., Naito T. Tetrahedron. 54:1998;15589 (k) Pahl A., Wartchow R., Meyer H.H. Tetrahedron Lett. 39:1998;2095 (l) Bailey P.D., Millwood P.A., Smith P.D. J. Chem. Soc. Chem. Commun. 1998;633 (m) Bayquen A.V., Read R.W. Tetrahedron. 52:1996;13467 (n) Altenbach H.-J., Himmeldirk K. Tetrahedron: Asymmetry. 6:1995;1077 (o) Nukui S., Sodeoka M., Sasai H., Shibasaki M. J. Org. Chem. 60:1995;398 (p) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575.
30. (a) Toyooka N., Yoshida Y., Yotsui Y., Momose T. J. Org. Chem. 64:1999;4914.
31. (b) Momose T., Toyooka N., Jin M. J. Chem. Soc., Perkin Trans. 1. 1997;2005.
32. (c) Toyooka N., Yoshida Y., Momose T. Tetrahedron Lett. 36:1995;3715.
33. (d) Momose T., Toyooka N. Tetrahedron Lett. 34:1993;5785.
34. (e) Momose T., Toyooka N., Jin M. Tetrahedron Lett. 33:1992;5389.
35. For synthesis of prosophylline and/or desoxoprosophylline, see: (a) Jourdant A., Zhu J. Tetrahedron Lett. 42:2001;3431 (b) Koulocheri S.D., Magiatis P., Haroutounian S.A. J. Org. Chem. 66:2001;7915 (c) Datta A., Kumar J.S.R., Roy S. Tetrahedron. 57:2001;1169 (d) Koulocheri S.D., Haroutounian S.A. Tetrahedron Lett. 40:1999;6869 (e) Yang C., Liao L., Xu Y., Zhang H., Xia P., Zhou W. Tetrahedron: Asymmetry. 10:1999;2311 (f) Koulocheri S.D., Haroutounian S.A. Synthesis. 1999;1889 (g) Herdeis C., Telser J. Eur. J. Org. Chem. 1999;1407 (h) Yang C.-F., Xu Y.-M., Liao L.-X., Zhou W.-S. Tetrahedron Lett. 39:1998;9227 (i) Ojima I., Vidal E.S. J. Org. Chem. 63:1998;7999 (j) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron: Asymmetry. 8:1997;3887 (k) Lucker T., Hiemstra H., Speckamp W.N. J. Org. Chem. 62:1997;3592 (l) Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Tadano K., Ogawa S. Tetrahedron. 50:1994;5681 (m) Tadano K., Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Ogawa S. Synlett. 1993;565 (n) Natume M., Ogawa M. Heterocycles. 16:1981;973 (o) Saitoh Y., Moriyama Y., Hirota H., Takahashi T., Khuong-Huu Q. Bull. Chem. Soc. Jpn. 54:1981;488 (p) Saitoh Y., Moriyama Y., Takahashi T., Khuong-Huu Q. Tetrahedron Lett. 1980;75.
36. For synthesis of prosophylline and/or desoxoprosophylline, see: (a) Jourdant A., Zhu J. Tetrahedron Lett. 42:2001;3431 (b) Koulocheri S.D., Magiatis P., Haroutounian S.A. J. Org. Chem. 66:2001;7915 (c) Datta A., Kumar J.S.R., Roy S. Tetrahedron. 57:2001;1169 (d) Koulocheri S.D., Haroutounian S.A. Tetrahedron Lett. 40:1999;6869 (e) Yang C., Liao L., Xu Y., Zhang H., Xia P., Zhou W. Tetrahedron: Asymmetry. 10:1999;2311 (f) Koulocheri S.D., Haroutounian S.A. Synthesis. 1999;1889 (g) Herdeis C., Telser J. Eur. J. Org. Chem. 1999;1407 (h) Yang C.-F., Xu Y.-M., Liao L.-X., Zhou W.-S. Tetrahedron Lett. 39:1998;9227 (i) Ojima I., Vidal E.S. J. Org. Chem. 63:1998;7999 (j) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron: Asymmetry. 8:1997;3887 (k) Lucker T., Hiemstra H., Speckamp W.N. J. Org. Chem. 62:1997;3592 (l) Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Tadano K., Ogawa S. Tetrahedron. 50:1994;5681 (m) Tadano K., Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Ogawa S. Synlett. 1993;565 (n) Natume M., Ogawa M. Heterocycles. 16:1981;973 (o) Saitoh Y., Moriyama Y., Hirota H., Takahashi T., Khuong-Huu Q. Bull. Chem. Soc. Jpn. 54:1981;488 (p) Saitoh Y., Moriyama Y., Takahashi T., Khuong-Huu Q. Tetrahedron Lett. 1980;75.
37. For synthesis of prosophylline and/or desoxoprosophylline, see: (a) Jourdant A., Zhu J. Tetrahedron Lett. 42:2001;3431 (b) Koulocheri S.D., Magiatis P., Haroutounian S.A. J. Org. Chem. 66:2001;7915 (c) Datta A., Kumar J.S.R., Roy S. Tetrahedron. 57:2001;1169 (d) Koulocheri S.D., Haroutounian S.A. Tetrahedron Lett. 40:1999;6869 (e) Yang C., Liao L., Xu Y., Zhang H., Xia P., Zhou W. Tetrahedron: Asymmetry. 10:1999;2311 (f) Koulocheri S.D., Haroutounian S.A. Synthesis. 1999;1889 (g) Herdeis C., Telser J. Eur. J. Org. Chem. 1999;1407 (h) Yang C.-F., Xu Y.-M., Liao L.-X., Zhou W.-S. Tetrahedron Lett. 39:1998;9227 (i) Ojima I., Vidal E.S. J. Org. Chem. 63:1998;7999 (j) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron: Asymmetry. 8:1997;3887 (k) Lucker T., Hiemstra H., Speckamp W.N. J. Org. Chem. 62:1997;3592 (l) Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Tadano K., Ogawa S. Tetrahedron. 50:1994;5681 (m) Tadano K., Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Ogawa S. Synlett. 1993;565 (n) Natume M., Ogawa M. Heterocycles. 16:1981;973 (o) Saitoh Y., Moriyama Y., Hirota H., Takahashi T., Khuong-Huu Q. Bull. Chem. Soc. Jpn. 54:1981;488 (p) Saitoh Y., Moriyama Y., Takahashi T., Khuong-Huu Q. Tetrahedron Lett. 1980;75.
38. For synthesis of prosophylline and/or desoxoprosophylline, see: (a) Jourdant A., Zhu J. Tetrahedron Lett. 42:2001;3431 (b) Koulocheri S.D., Magiatis P., Haroutounian S.A. J. Org. Chem. 66:2001;7915 (c) Datta A., Kumar J.S.R., Roy S. Tetrahedron. 57:2001;1169 (d) Koulocheri S.D., Haroutounian S.A. Tetrahedron Lett. 40:1999;6869 (e) Yang C., Liao L., Xu Y., Zhang H., Xia P., Zhou W. Tetrahedron: Asymmetry. 10:1999;2311 (f) Koulocheri S.D., Haroutounian S.A. Synthesis. 1999;1889 (g) Herdeis C., Telser J. Eur. J. Org. Chem. 1999;1407 (h) Yang C.-F., Xu Y.-M., Liao L.-X., Zhou W.-S. Tetrahedron Lett. 39:1998;9227 (i) Ojima I., Vidal E.S. J. Org. Chem. 63:1998;7999 (j) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron: Asymmetry. 8:1997;3887 (k) Lucker T., Hiemstra H., Speckamp W.N. J. Org. Chem. 62:1997;3592 (l) Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Tadano K., Ogawa S. Tetrahedron. 50:1994;5681 (m) Tadano K., Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Ogawa S. Synlett. 1993;565 (n) Natume M., Ogawa M. Heterocycles. 16:1981;973 (o) Saitoh Y., Moriyama Y., Hirota H., Takahashi T., Khuong-Huu Q. Bull. Chem. Soc. Jpn. 54:1981;488 (p) Saitoh Y., Moriyama Y., Takahashi T., Khuong-Huu Q. Tetrahedron Lett. 1980;75.
39. For synthesis of prosophylline and/or desoxoprosophylline, see: (a) Jourdant A., Zhu J. Tetrahedron Lett. 42:2001;3431 (b) Koulocheri S.D., Magiatis P., Haroutounian S.A. J. Org. Chem. 66:2001;7915 (c) Datta A., Kumar J.S.R., Roy S. Tetrahedron. 57:2001;1169 (d) Koulocheri S.D., Haroutounian S.A. Tetrahedron Lett. 40:1999;6869 (e) Yang C., Liao L., Xu Y., Zhang H., Xia P., Zhou W. Tetrahedron: Asymmetry. 10:1999;2311 (f) Koulocheri S.D., Haroutounian S.A. Synthesis. 1999;1889 (g) Herdeis C., Telser J. Eur. J. Org. Chem. 1999;1407 (h) Yang C.-F., Xu Y.-M., Liao L.-X., Zhou W.-S. Tetrahedron Lett. 39:1998;9227 (i) Ojima I., Vidal E.S. J. Org. Chem. 63:1998;7999 (j) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron: Asymmetry. 8:1997;3887 (k) Lucker T., Hiemstra H., Speckamp W.N. J. Org. Chem. 62:1997;3592 (l) Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Tadano K., Ogawa S. Tetrahedron. 50:1994;5681 (m) Tadano K., Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Ogawa S. Synlett. 1993;565 (n) Natume M., Ogawa M. Heterocycles. 16:1981;973 (o) Saitoh Y., Moriyama Y., Hirota H., Takahashi T., Khuong-Huu Q. Bull. Chem. Soc. Jpn. 54:1981;488 (p) Saitoh Y., Moriyama Y., Takahashi T., Khuong-Huu Q. Tetrahedron Lett. 1980;75.
40. For synthesis of prosophylline and/or desoxoprosophylline, see: (a) Jourdant A., Zhu J. Tetrahedron Lett. 42:2001;3431 (b) Koulocheri S.D., Magiatis P., Haroutounian S.A. J. Org. Chem. 66:2001;7915 (c) Datta A., Kumar J.S.R., Roy S. Tetrahedron. 57:2001;1169 (d) Koulocheri S.D., Haroutounian S.A. Tetrahedron Lett. 40:1999;6869 (e) Yang C., Liao L., Xu Y., Zhang H., Xia P., Zhou W. Tetrahedron: Asymmetry. 10:1999;2311 (f) Koulocheri S.D., Haroutounian S.A. Synthesis. 1999;1889 (g) Herdeis C., Telser J. Eur. J. Org. Chem. 1999;1407 (h) Yang C.-F., Xu Y.-M., Liao L.-X., Zhou W.-S. Tetrahedron Lett. 39:1998;9227 (i) Ojima I., Vidal E.S. J. Org. Chem. 63:1998;7999 (j) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron: Asymmetry. 8:1997;3887 (k) Lucker T., Hiemstra H., Speckamp W.N. J. Org. Chem. 62:1997;3592 (l) Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Tadano K., Ogawa S. Tetrahedron. 50:1994;5681 (m) Tadano K., Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Ogawa S. Synlett. 1993;565 (n) Natume M., Ogawa M. Heterocycles. 16:1981;973 (o) Saitoh Y., Moriyama Y., Hirota H., Takahashi T., Khuong-Huu Q. Bull. Chem. Soc. Jpn. 54:1981;488 (p) Saitoh Y., Moriyama Y., Takahashi T., Khuong-Huu Q. Tetrahedron Lett. 1980;75.
41. For synthesis of prosophylline and/or desoxoprosophylline, see: (a) Jourdant A., Zhu J. Tetrahedron Lett. 42:2001;3431 (b) Koulocheri S.D., Magiatis P., Haroutounian S.A. J. Org. Chem. 66:2001;7915 (c) Datta A., Kumar J.S.R., Roy S. Tetrahedron. 57:2001;1169 (d) Koulocheri S.D., Haroutounian S.A. Tetrahedron Lett. 40:1999;6869 (e) Yang C., Liao L., Xu Y., Zhang H., Xia P., Zhou W. Tetrahedron: Asymmetry. 10:1999;2311 (f) Koulocheri S.D., Haroutounian S.A. Synthesis. 1999;1889 (g) Herdeis C., Telser J. Eur. J. Org. Chem. 1999;1407 (h) Yang C.-F., Xu Y.-M., Liao L.-X., Zhou W.-S. Tetrahedron Lett. 39:1998;9227 (i) Ojima I., Vidal E.S. J. Org. Chem. 63:1998;7999 (j) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron: Asymmetry. 8:1997;3887 (k) Lucker T., Hiemstra H., Speckamp W.N. J. Org. Chem. 62:1997;3592 (l) Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Tadano K., Ogawa S. Tetrahedron. 50:1994;5681 (m) Tadano K., Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Ogawa S. Synlett. 1993;565 (n) Natume M., Ogawa M. Heterocycles. 16:1981;973 (o) Saitoh Y., Moriyama Y., Hirota H., Takahashi T., Khuong-Huu Q. Bull. Chem. Soc. Jpn. 54:1981;488 (p) Saitoh Y., Moriyama Y., Takahashi T., Khuong-Huu Q. Tetrahedron Lett. 1980;75.
42. For synthesis of prosophylline and/or desoxoprosophylline, see: (a) Jourdant A., Zhu J. Tetrahedron Lett. 42:2001;3431 (b) Koulocheri S.D., Magiatis P., Haroutounian S.A. J. Org. Chem. 66:2001;7915 (c) Datta A., Kumar J.S.R., Roy S. Tetrahedron. 57:2001;1169 (d) Koulocheri S.D., Haroutounian S.A. Tetrahedron Lett. 40:1999;6869 (e) Yang C., Liao L., Xu Y., Zhang H., Xia P., Zhou W. Tetrahedron: Asymmetry. 10:1999;2311 (f) Koulocheri S.D., Haroutounian S.A. Synthesis. 1999;1889 (g) Herdeis C., Telser J. Eur. J. Org. Chem. 1999;1407 (h) Yang C.-F., Xu Y.-M., Liao L.-X., Zhou W.-S. Tetrahedron Lett. 39:1998;9227 (i) Ojima I., Vidal E.S. J. Org. Chem. 63:1998;7999 (j) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron: Asymmetry. 8:1997;3887 (k) Lucker T., Hiemstra H., Speckamp W.N. J. Org. Chem. 62:1997;3592 (l) Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Tadano K., Ogawa S. Tetrahedron. 50:1994;5681 (m) Tadano K., Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Ogawa S. Synlett. 1993;565 (n) Natume M., Ogawa M. Heterocycles. 16:1981;973 (o) Saitoh Y., Moriyama Y., Hirota H., Takahashi T., Khuong-Huu Q. Bull. Chem. Soc. Jpn. 54:1981;488 (p) Saitoh Y., Moriyama Y., Takahashi T., Khuong-Huu Q. Tetrahedron Lett. 1980;75.
43. For synthesis of prosophylline and/or desoxoprosophylline, see: (a) Jourdant A., Zhu J. Tetrahedron Lett. 42:2001;3431 (b) Koulocheri S.D., Magiatis P., Haroutounian S.A. J. Org. Chem. 66:2001;7915 (c) Datta A., Kumar J.S.R., Roy S. Tetrahedron. 57:2001;1169 (d) Koulocheri S.D., Haroutounian S.A. Tetrahedron Lett. 40:1999;6869 (e) Yang C., Liao L., Xu Y., Zhang H., Xia P., Zhou W. Tetrahedron: Asymmetry. 10:1999;2311 (f) Koulocheri S.D., Haroutounian S.A. Synthesis. 1999;1889 (g) Herdeis C., Telser J. Eur. J. Org. Chem. 1999;1407 (h) Yang C.-F., Xu Y.-M., Liao L.-X., Zhou W.-S. Tetrahedron Lett. 39:1998;9227 (i) Ojima I., Vidal E.S. J. Org. Chem. 63:1998;7999 (j) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron: Asymmetry. 8:1997;3887 (k) Lucker T., Hiemstra H., Speckamp W.N. J. Org. Chem. 62:1997;3592 (l) Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Tadano K., Ogawa S. Tetrahedron. 50:1994;5681 (m) Tadano K., Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Ogawa S. Synlett. 1993;565 (n) Natume M., Ogawa M. Heterocycles. 16:1981;973 (o) Saitoh Y., Moriyama Y., Hirota H., Takahashi T., Khuong-Huu Q. Bull. Chem. Soc. Jpn. 54:1981;488 (p) Saitoh Y., Moriyama Y., Takahashi T., Khuong-Huu Q. Tetrahedron Lett. 1980;75.
44. For synthesis of prosophylline and/or desoxoprosophylline, see: (a) Jourdant A., Zhu J. Tetrahedron Lett. 42:2001;3431 (b) Koulocheri S.D., Magiatis P., Haroutounian S.A. J. Org. Chem. 66:2001;7915 (c) Datta A., Kumar J.S.R., Roy S. Tetrahedron. 57:2001;1169 (d) Koulocheri S.D., Haroutounian S.A. Tetrahedron Lett. 40:1999;6869 (e) Yang C., Liao L., Xu Y., Zhang H., Xia P., Zhou W. Tetrahedron: Asymmetry. 10:1999;2311 (f) Koulocheri S.D., Haroutounian S.A. Synthesis. 1999;1889 (g) Herdeis C., Telser J. Eur. J. Org. Chem. 1999;1407 (h) Yang C.-F., Xu Y.-M., Liao L.-X., Zhou W.-S. Tetrahedron Lett. 39:1998;9227 (i) Ojima I., Vidal E.S. J. Org. Chem. 63:1998;7999 (j) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron: Asymmetry. 8:1997;3887 (k) Lucker T., Hiemstra H., Speckamp W.N. J. Org. Chem. 62:1997;3592 (l) Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Tadano K., Ogawa S. Tetrahedron. 50:1994;5681 (m) Tadano K., Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Ogawa S. Synlett. 1993;565 (n) Natume M., Ogawa M. Heterocycles. 16:1981;973 (o) Saitoh Y., Moriyama Y., Hirota H., Takahashi T., Khuong-Huu Q. Bull. Chem. Soc. Jpn. 54:1981;488 (p) Saitoh Y., Moriyama Y., Takahashi T., Khuong-Huu Q. Tetrahedron Lett. 1980;75.
45. For synthesis of prosophylline and/or desoxoprosophylline, see: (a) Jourdant A., Zhu J. Tetrahedron Lett. 42:2001;3431 (b) Koulocheri S.D., Magiatis P., Haroutounian S.A. J. Org. Chem. 66:2001;7915 (c) Datta A., Kumar J.S.R., Roy S. Tetrahedron. 57:2001;1169 (d) Koulocheri S.D., Haroutounian S.A. Tetrahedron Lett. 40:1999;6869 (e) Yang C., Liao L., Xu Y., Zhang H., Xia P., Zhou W. Tetrahedron: Asymmetry. 10:1999;2311 (f) Koulocheri S.D., Haroutounian S.A. Synthesis. 1999;1889 (g) Herdeis C., Telser J. Eur. J. Org. Chem. 1999;1407 (h) Yang C.-F., Xu Y.-M., Liao L.-X., Zhou W.-S. Tetrahedron Lett. 39:1998;9227 (i) Ojima I., Vidal E.S. J. Org. Chem. 63:1998;7999 (j) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron: Asymmetry. 8:1997;3887 (k) Lucker T., Hiemstra H., Speckamp W.N. J. Org. Chem. 62:1997;3592 (l) Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Tadano K., Ogawa S. Tetrahedron. 50:1994;5681 (m) Tadano K., Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Ogawa S. Synlett. 1993;565 (n) Natume M., Ogawa M. Heterocycles. 16:1981;973 (o) Saitoh Y., Moriyama Y., Hirota H., Takahashi T., Khuong-Huu Q. Bull. Chem. Soc. Jpn. 54:1981;488 (p) Saitoh Y., Moriyama Y., Takahashi T., Khuong-Huu Q. Tetrahedron Lett. 1980;75.
46. For synthesis of prosophylline and/or desoxoprosophylline, see: (a) Jourdant A., Zhu J. Tetrahedron Lett. 42:2001;3431 (b) Koulocheri S.D., Magiatis P., Haroutounian S.A. J. Org. Chem. 66:2001;7915 (c) Datta A., Kumar J.S.R., Roy S. Tetrahedron. 57:2001;1169 (d) Koulocheri S.D., Haroutounian S.A. Tetrahedron Lett. 40:1999;6869 (e) Yang C., Liao L., Xu Y., Zhang H., Xia P., Zhou W. Tetrahedron: Asymmetry. 10:1999;2311 (f) Koulocheri S.D., Haroutounian S.A. Synthesis. 1999;1889 (g) Herdeis C., Telser J. Eur. J. Org. Chem. 1999;1407 (h) Yang C.-F., Xu Y.-M., Liao L.-X., Zhou W.-S. Tetrahedron Lett. 39:1998;9227 (i) Ojima I., Vidal E.S. J. Org. Chem. 63:1998;7999 (j) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron: Asymmetry. 8:1997;3887 (k) Lucker T., Hiemstra H., Speckamp W.N. J. Org. Chem. 62:1997;3592 (l) Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Tadano K., Ogawa S. Tetrahedron. 50:1994;5681 (m) Tadano K., Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Ogawa S. Synlett. 1993;565 (n) Natume M., Ogawa M. Heterocycles. 16:1981;973 (o) Saitoh Y., Moriyama Y., Hirota H., Takahashi T., Khuong-Huu Q. Bull. Chem. Soc. Jpn. 54:1981;488 (p) Saitoh Y., Moriyama Y., Takahashi T., Khuong-Huu Q. Tetrahedron Lett. 1980;75.
47. For synthesis of prosophylline and/or desoxoprosophylline, see: (a) Jourdant A., Zhu J. Tetrahedron Lett. 42:2001;3431 (b) Koulocheri S.D., Magiatis P., Haroutounian S.A. J. Org. Chem. 66:2001;7915 (c) Datta A., Kumar J.S.R., Roy S. Tetrahedron. 57:2001;1169 (d) Koulocheri S.D., Haroutounian S.A. Tetrahedron Lett. 40:1999;6869 (e) Yang C., Liao L., Xu Y., Zhang H., Xia P., Zhou W. Tetrahedron: Asymmetry. 10:1999;2311 (f) Koulocheri S.D., Haroutounian S.A. Synthesis. 1999;1889 (g) Herdeis C., Telser J. Eur. J. Org. Chem. 1999;1407 (h) Yang C.-F., Xu Y.-M., Liao L.-X., Zhou W.-S. Tetrahedron Lett. 39:1998;9227 (i) Ojima I., Vidal E.S. J. Org. Chem. 63:1998;7999 (j) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron: Asymmetry. 8:1997;3887 (k) Lucker T., Hiemstra H., Speckamp W.N. J. Org. Chem. 62:1997;3592 (l) Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Tadano K., Ogawa S. Tetrahedron. 50:1994;5681 (m) Tadano K., Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Ogawa S. Synlett. 1993;565 (n) Natume M., Ogawa M. Heterocycles. 16:1981;973 (o) Saitoh Y., Moriyama Y., Hirota H., Takahashi T., Khuong-Huu Q. Bull. Chem. Soc. Jpn. 54:1981;488 (p) Saitoh Y., Moriyama Y., Takahashi T., Khuong-Huu Q. Tetrahedron Lett. 1980;75.
48. For synthesis of prosophylline and/or desoxoprosophylline, see: (a) Jourdant A., Zhu J. Tetrahedron Lett. 42:2001;3431 (b) Koulocheri S.D., Magiatis P., Haroutounian S.A. J. Org. Chem. 66:2001;7915 (c) Datta A., Kumar J.S.R., Roy S. Tetrahedron. 57:2001;1169 (d) Koulocheri S.D., Haroutounian S.A. Tetrahedron Lett. 40:1999;6869 (e) Yang C., Liao L., Xu Y., Zhang H., Xia P., Zhou W. Tetrahedron: Asymmetry. 10:1999;2311 (f) Koulocheri S.D., Haroutounian S.A. Synthesis. 1999;1889 (g) Herdeis C., Telser J. Eur. J. Org. Chem. 1999;1407 (h) Yang C.-F., Xu Y.-M., Liao L.-X., Zhou W.-S. Tetrahedron Lett. 39:1998;9227 (i) Ojima I., Vidal E.S. J. Org. Chem. 63:1998;7999 (j) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron: Asymmetry. 8:1997;3887 (k) Lucker T., Hiemstra H., Speckamp W.N. J. Org. Chem. 62:1997;3592 (l) Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Tadano K., Ogawa S. Tetrahedron. 50:1994;5681 (m) Tadano K., Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Ogawa S. Synlett. 1993;565 (n) Natume M., Ogawa M. Heterocycles. 16:1981;973 (o) Saitoh Y., Moriyama Y., Hirota H., Takahashi T., Khuong-Huu Q. Bull. Chem. Soc. Jpn. 54:1981;488 (p) Saitoh Y., Moriyama Y., Takahashi T., Khuong-Huu Q. Tetrahedron Lett. 1980;75.
49. For synthesis of prosophylline and/or desoxoprosophylline, see: (a) Jourdant A., Zhu J. Tetrahedron Lett. 42:2001;3431 (b) Koulocheri S.D., Magiatis P., Haroutounian S.A. J. Org. Chem. 66:2001;7915 (c) Datta A., Kumar J.S.R., Roy S. Tetrahedron. 57:2001;1169 (d) Koulocheri S.D., Haroutounian S.A. Tetrahedron Lett. 40:1999;6869 (e) Yang C., Liao L., Xu Y., Zhang H., Xia P., Zhou W. Tetrahedron: Asymmetry. 10:1999;2311 (f) Koulocheri S.D., Haroutounian S.A. Synthesis. 1999;1889 (g) Herdeis C., Telser J. Eur. J. Org. Chem. 1999;1407 (h) Yang C.-F., Xu Y.-M., Liao L.-X., Zhou W.-S. Tetrahedron Lett. 39:1998;9227 (i) Ojima I., Vidal E.S. J. Org. Chem. 63:1998;7999 (j) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron: Asymmetry. 8:1997;3887 (k) Lucker T., Hiemstra H., Speckamp W.N. J. Org. Chem. 62:1997;3592 (l) Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Tadano K., Ogawa S. Tetrahedron. 50:1994;5681 (m) Tadano K., Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Ogawa S. Synlett. 1993;565 (n) Natume M., Ogawa M. Heterocycles. 16:1981;973 (o) Saitoh Y., Moriyama Y., Hirota H., Takahashi T., Khuong-Huu Q. Bull. Chem. Soc. Jpn. 54:1981;488 (p) Saitoh Y., Moriyama Y., Takahashi T., Khuong-Huu Q. Tetrahedron Lett. 1980;75.
50. For synthesis of prosophylline and/or desoxoprosophylline, see: (a) Jourdant A., Zhu J. Tetrahedron Lett. 42:2001;3431 (b) Koulocheri S.D., Magiatis P., Haroutounian S.A. J. Org. Chem. 66:2001;7915 (c) Datta A., Kumar J.S.R., Roy S. Tetrahedron. 57:2001;1169 (d) Koulocheri S.D., Haroutounian S.A. Tetrahedron Lett. 40:1999;6869 (e) Yang C., Liao L., Xu Y., Zhang H., Xia P., Zhou W. Tetrahedron: Asymmetry. 10:1999;2311 (f) Koulocheri S.D., Haroutounian S.A. Synthesis. 1999;1889 (g) Herdeis C., Telser J. Eur. J. Org. Chem. 1999;1407 (h) Yang C.-F., Xu Y.-M., Liao L.-X., Zhou W.-S. Tetrahedron Lett. 39:1998;9227 (i) Ojima I., Vidal E.S. J. Org. Chem. 63:1998;7999 (j) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron: Asymmetry. 8:1997;3887 (k) Lucker T., Hiemstra H., Speckamp W.N. J. Org. Chem. 62:1997;3592 (l) Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Tadano K., Ogawa S. Tetrahedron. 50:1994;5681 (m) Tadano K., Takao K., Nigawara Y., Nishio E., Takagi I., Maeda K., Ogawa S. Synlett. 1993;565 (n) Natume M., Ogawa M. Heterocycles. 16:1981;973 (o) Saitoh Y., Moriyama Y., Hirota H., Takahashi T., Khuong-Huu Q. Bull. Chem. Soc. Jpn. 54:1981;488 (p) Saitoh Y., Moriyama Y., Takahashi T., Khuong-Huu Q. Tetrahedron Lett. 1980;75.
51. For synthesis of prosopinine and/or desoxoprosopinine: (a) Ref. 5b. (b) Enders D., Kirchhoff J.H. Synthesis. 2000;2099 (c) Ref. 5e. (d) Agami C., County F., Lam H., Mathieu H. Tetrahedron. 54:1998;8783 (e) Agami C., County F., Mathieu H. Tetrahedron Lett. 39:1998;3505 (f) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron Lett. 38:1997;7469 (g) Ref. 5j. (h) Hirai Y., Watanabe J., Nozaki T., Yokoyama H., Yamaguchi S. J. Org. Chem. 62:1997;776 (i) Yuasa Y., Ando J., Shibuya S. J. Chem. Soc., Perkin Trans. 1. 1996;793 (j) Yuasa Y., Ando J., Shibuya S. Tetrahedron: Asymmetry. 6:1995;1525 (k) Ref. 5l. (l) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575 (m) Cook G.R., Beholz L.G., Stille J.R. Tetrahedron Lett. 35:1994;1669 (n) Ref. 5m. (o) Ciufolini M.A., Hermann C.W., Whitmire K.H., Byrne N.E. J. Am. Chem. Soc. 111:1989;3473 (p) Holmes A.B., Thompson J., Baxter A.J.G., Dixon J. J. Chem. Soc., Chem. Commun. 1985;37 (q) Ref. 5o. (r) Ref. 5p.
52. For synthesis of prosopinine and/or desoxoprosopinine: (a) Ref. 5b. (b) Enders D., Kirchhoff J.H. Synthesis. 2000;2099 (c) Ref. 5e. (d) Agami C., County F., Lam H., Mathieu H. Tetrahedron. 54:1998;8783 (e) Agami C., County F., Mathieu H. Tetrahedron Lett. 39:1998;3505 (f) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron Lett. 38:1997;7469 (g) Ref. 5j. (h) Hirai Y., Watanabe J., Nozaki T., Yokoyama H., Yamaguchi S. J. Org. Chem. 62:1997;776 (i) Yuasa Y., Ando J., Shibuya S. J. Chem. Soc., Perkin Trans. 1. 1996;793 (j) Yuasa Y., Ando J., Shibuya S. Tetrahedron: Asymmetry. 6:1995;1525 (k) Ref. 5l. (l) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575 (m) Cook G.R., Beholz L.G., Stille J.R. Tetrahedron Lett. 35:1994;1669 (n) Ref. 5m. (o) Ciufolini M.A., Hermann C.W., Whitmire K.H., Byrne N.E. J. Am. Chem. Soc. 111:1989;3473 (p) Holmes A.B., Thompson J., Baxter A.J.G., Dixon J. J. Chem. Soc., Chem. Commun. 1985;37 (q) Ref. 5o. (r) Ref. 5p.
53. For synthesis of prosopinine and/or desoxoprosopinine: (a) Ref. 5b. (b) Enders D., Kirchhoff J.H. Synthesis. 2000;2099 (c) Ref. 5e. (d) Agami C., County F., Lam H., Mathieu H. Tetrahedron. 54:1998;8783 (e) Agami C., County F., Mathieu H. Tetrahedron Lett. 39:1998;3505 (f) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron Lett. 38:1997;7469 (g) Ref. 5j. (h) Hirai Y., Watanabe J., Nozaki T., Yokoyama H., Yamaguchi S. J. Org. Chem. 62:1997;776 (i) Yuasa Y., Ando J., Shibuya S. J. Chem. Soc., Perkin Trans. 1. 1996;793 (j) Yuasa Y., Ando J., Shibuya S. Tetrahedron: Asymmetry. 6:1995;1525 (k) Ref. 5l. (l) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575 (m) Cook G.R., Beholz L.G., Stille J.R. Tetrahedron Lett. 35:1994;1669 (n) Ref. 5m. (o) Ciufolini M.A., Hermann C.W., Whitmire K.H., Byrne N.E. J. Am. Chem. Soc. 111:1989;3473 (p) Holmes A.B., Thompson J., Baxter A.J.G., Dixon J. J. Chem. Soc., Chem. Commun. 1985;37 (q) Ref. 5o. (r) Ref. 5p.
54. For synthesis of prosopinine and/or desoxoprosopinine: (a) Ref. 5b. (b) Enders D., Kirchhoff J.H. Synthesis. 2000;2099 (c) Ref. 5e. (d) Agami C., County F., Lam H., Mathieu H. Tetrahedron. 54:1998;8783 (e) Agami C., County F., Mathieu H. Tetrahedron Lett. 39:1998;3505 (f) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron Lett. 38:1997;7469 (g) Ref. 5j. (h) Hirai Y., Watanabe J., Nozaki T., Yokoyama H., Yamaguchi S. J. Org. Chem. 62:1997;776 (i) Yuasa Y., Ando J., Shibuya S. J. Chem. Soc., Perkin Trans. 1. 1996;793 (j) Yuasa Y., Ando J., Shibuya S. Tetrahedron: Asymmetry. 6:1995;1525 (k) Ref. 5l. (l) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575 (m) Cook G.R., Beholz L.G., Stille J.R. Tetrahedron Lett. 35:1994;1669 (n) Ref. 5m. (o) Ciufolini M.A., Hermann C.W., Whitmire K.H., Byrne N.E. J. Am. Chem. Soc. 111:1989;3473 (p) Holmes A.B., Thompson J., Baxter A.J.G., Dixon J. J. Chem. Soc., Chem. Commun. 1985;37 (q) Ref. 5o. (r) Ref. 5p.
55. For synthesis of prosopinine and/or desoxoprosopinine: (a) Ref. 5b. (b) Enders D., Kirchhoff J.H. Synthesis. 2000;2099 (c) Ref. 5e. (d) Agami C., County F., Lam H., Mathieu H. Tetrahedron. 54:1998;8783 (e) Agami C., County F., Mathieu H. Tetrahedron Lett. 39:1998;3505 (f) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron Lett. 38:1997;7469 (g) Ref. 5j. (h) Hirai Y., Watanabe J., Nozaki T., Yokoyama H., Yamaguchi S. J. Org. Chem. 62:1997;776 (i) Yuasa Y., Ando J., Shibuya S. J. Chem. Soc., Perkin Trans. 1. 1996;793 (j) Yuasa Y., Ando J., Shibuya S. Tetrahedron: Asymmetry. 6:1995;1525 (k) Ref. 5l. (l) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575 (m) Cook G.R., Beholz L.G., Stille J.R. Tetrahedron Lett. 35:1994;1669 (n) Ref. 5m. (o) Ciufolini M.A., Hermann C.W., Whitmire K.H., Byrne N.E. J. Am. Chem. Soc. 111:1989;3473 (p) Holmes A.B., Thompson J., Baxter A.J.G., Dixon J. J. Chem. Soc., Chem. Commun. 1985;37 (q) Ref. 5o. (r) Ref. 5p.
56. For synthesis of prosopinine and/or desoxoprosopinine: (a) Ref. 5b. (b) Enders D., Kirchhoff J.H. Synthesis. 2000;2099 (c) Ref. 5e. (d) Agami C., County F., Lam H., Mathieu H. Tetrahedron. 54:1998;8783 (e) Agami C., County F., Mathieu H. Tetrahedron Lett. 39:1998;3505 (f) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron Lett. 38:1997;7469 (g) Ref. 5j. (h) Hirai Y., Watanabe J., Nozaki T., Yokoyama H., Yamaguchi S. J. Org. Chem. 62:1997;776 (i) Yuasa Y., Ando J., Shibuya S. J. Chem. Soc., Perkin Trans. 1. 1996;793 (j) Yuasa Y., Ando J., Shibuya S. Tetrahedron: Asymmetry. 6:1995;1525 (k) Ref. 5l. (l) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575 (m) Cook G.R., Beholz L.G., Stille J.R. Tetrahedron Lett. 35:1994;1669 (n) Ref. 5m. (o) Ciufolini M.A., Hermann C.W., Whitmire K.H., Byrne N.E. J. Am. Chem. Soc. 111:1989;3473 (p) Holmes A.B., Thompson J., Baxter A.J.G., Dixon J. J. Chem. Soc., Chem. Commun. 1985;37 (q) Ref. 5o. (r) Ref. 5p.
57. For synthesis of prosopinine and/or desoxoprosopinine: (a) Ref. 5b. (b) Enders D., Kirchhoff J.H. Synthesis. 2000;2099 (c) Ref. 5e. (d) Agami C., County F., Lam H., Mathieu H. Tetrahedron. 54:1998;8783 (e) Agami C., County F., Mathieu H. Tetrahedron Lett. 39:1998;3505 (f) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron Lett. 38:1997;7469 (g) Ref. 5j. (h) Hirai Y., Watanabe J., Nozaki T., Yokoyama H., Yamaguchi S. J. Org. Chem. 62:1997;776 (i) Yuasa Y., Ando J., Shibuya S. J. Chem. Soc., Perkin Trans. 1. 1996;793 (j) Yuasa Y., Ando J., Shibuya S. Tetrahedron: Asymmetry. 6:1995;1525 (k) Ref. 5l. (l) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575 (m) Cook G.R., Beholz L.G., Stille J.R. Tetrahedron Lett. 35:1994;1669 (n) Ref. 5m. (o) Ciufolini M.A., Hermann C.W., Whitmire K.H., Byrne N.E. J. Am. Chem. Soc. 111:1989;3473 (p) Holmes A.B., Thompson J., Baxter A.J.G., Dixon J. J. Chem. Soc., Chem. Commun. 1985;37 (q) Ref. 5o. (r) Ref. 5p.
58. For synthesis of prosopinine and/or desoxoprosopinine: (a) Ref. 5b. (b) Enders D., Kirchhoff J.H. Synthesis. 2000;2099 (c) Ref. 5e. (d) Agami C., County F., Lam H., Mathieu H. Tetrahedron. 54:1998;8783 (e) Agami C., County F., Mathieu H. Tetrahedron Lett. 39:1998;3505 (f) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron Lett. 38:1997;7469 (g) Ref. 5j. (h) Hirai Y., Watanabe J., Nozaki T., Yokoyama H., Yamaguchi S. J. Org. Chem. 62:1997;776 (i) Yuasa Y., Ando J., Shibuya S. J. Chem. Soc., Perkin Trans. 1. 1996;793 (j) Yuasa Y., Ando J., Shibuya S. Tetrahedron: Asymmetry. 6:1995;1525 (k) Ref. 5l. (l) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575 (m) Cook G.R., Beholz L.G., Stille J.R. Tetrahedron Lett. 35:1994;1669 (n) Ref. 5m. (o) Ciufolini M.A., Hermann C.W., Whitmire K.H., Byrne N.E. J. Am. Chem. Soc. 111:1989;3473 (p) Holmes A.B., Thompson J., Baxter A.J.G., Dixon J. J. Chem. Soc., Chem. Commun. 1985;37 (q) Ref. 5o. (r) Ref. 5p.
59. For synthesis of prosopinine and/or desoxoprosopinine: (a) Ref. 5b. (b) Enders D., Kirchhoff J.H. Synthesis. 2000;2099 (c) Ref. 5e. (d) Agami C., County F., Lam H., Mathieu H. Tetrahedron. 54:1998;8783 (e) Agami C., County F., Mathieu H. Tetrahedron Lett. 39:1998;3505 (f) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron Lett. 38:1997;7469 (g) Ref. 5j. (h) Hirai Y., Watanabe J., Nozaki T., Yokoyama H., Yamaguchi S. J. Org. Chem. 62:1997;776 (i) Yuasa Y., Ando J., Shibuya S. J. Chem. Soc., Perkin Trans. 1. 1996;793 (j) Yuasa Y., Ando J., Shibuya S. Tetrahedron: Asymmetry. 6:1995;1525 (k) Ref. 5l. (l) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575 (m) Cook G.R., Beholz L.G., Stille J.R. Tetrahedron Lett. 35:1994;1669 (n) Ref. 5m. (o) Ciufolini M.A., Hermann C.W., Whitmire K.H., Byrne N.E. J. Am. Chem. Soc. 111:1989;3473 (p) Holmes A.B., Thompson J., Baxter A.J.G., Dixon J. J. Chem. Soc., Chem. Commun. 1985;37 (q) Ref. 5o. (r) Ref. 5p.
60. For synthesis of prosopinine and/or desoxoprosopinine: (a) Ref. 5b.
61. For synthesis of prosopinine and/or desoxoprosopinine: (a) Ref. 5b. (b) Enders D., Kirchhoff J.H. Synthesis. 2000;2099 (c) Ref. 5e. (d) Agami C., County F., Lam H., Mathieu H. Tetrahedron. 54:1998;8783 (e) Agami C., County F., Mathieu H. Tetrahedron Lett. 39:1998;3505 (f) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron Lett. 38:1997;7469 (g) Ref. 5j. (h) Hirai Y., Watanabe J., Nozaki T., Yokoyama H., Yamaguchi S. J. Org. Chem. 62:1997;776 (i) Yuasa Y., Ando J., Shibuya S. J. Chem. Soc., Perkin Trans. 1. 1996;793 (j) Yuasa Y., Ando J., Shibuya S. Tetrahedron: Asymmetry. 6:1995;1525 (k) Ref. 5l. (l) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575 (m) Cook G.R., Beholz L.G., Stille J.R. Tetrahedron Lett. 35:1994;1669 (n) Ref. 5m. (o) Ciufolini M.A., Hermann C.W., Whitmire K.H., Byrne N.E. J. Am. Chem. Soc. 111:1989;3473 (p) Holmes A.B., Thompson J., Baxter A.J.G., Dixon J. J. Chem. Soc., Chem. Commun. 1985;37 (q) Ref. 5o. (r) Ref. 5p.
62. For synthesis of prosopinine and/or desoxoprosopinine: (a) Ref. 5b. (b) Enders D., Kirchhoff J.H. Synthesis. 2000;2099 (c) Ref. 5e. (d) Agami C., County F., Lam H., Mathieu H. Tetrahedron. 54:1998;8783 (e) Agami C., County F., Mathieu H. Tetrahedron Lett. 39:1998;3505 (f) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron Lett. 38:1997;7469 (g) Ref. 5j. (h) Hirai Y., Watanabe J., Nozaki T., Yokoyama H., Yamaguchi S. J. Org. Chem. 62:1997;776 (i) Yuasa Y., Ando J., Shibuya S. J. Chem. Soc., Perkin Trans. 1. 1996;793 (j) Yuasa Y., Ando J., Shibuya S. Tetrahedron: Asymmetry. 6:1995;1525 (k) Ref. 5l. (l) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575 (m) Cook G.R., Beholz L.G., Stille J.R. Tetrahedron Lett. 35:1994;1669 (n) Ref. 5m. (o) Ciufolini M.A., Hermann C.W., Whitmire K.H., Byrne N.E. J. Am. Chem. Soc. 111:1989;3473 (p) Holmes A.B., Thompson J., Baxter A.J.G., Dixon J. J. Chem. Soc., Chem. Commun. 1985;37 (q) Ref. 5o. (r) Ref. 5p.
63. For synthesis of prosopinine and/or desoxoprosopinine: (a) Ref. 5b. (b) Enders D., Kirchhoff J.H. Synthesis. 2000;2099 (c) Ref. 5e. (d) Agami C., County F., Lam H., Mathieu H. Tetrahedron. 54:1998;8783 (e) Agami C., County F., Mathieu H. Tetrahedron Lett. 39:1998;3505 (f) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron Lett. 38:1997;7469 (g) Ref. 5j. (h) Hirai Y., Watanabe J., Nozaki T., Yokoyama H., Yamaguchi S. J. Org. Chem. 62:1997;776 (i) Yuasa Y., Ando J., Shibuya S. J. Chem. Soc., Perkin Trans. 1. 1996;793 (j) Yuasa Y., Ando J., Shibuya S. Tetrahedron: Asymmetry. 6:1995;1525 (k) Ref. 5l. (l) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575 (m) Cook G.R., Beholz L.G., Stille J.R. Tetrahedron Lett. 35:1994;1669 (n) Ref. 5m. (o) Ciufolini M.A., Hermann C.W., Whitmire K.H., Byrne N.E. J. Am. Chem. Soc. 111:1989;3473 (p) Holmes A.B., Thompson J., Baxter A.J.G., Dixon J. J. Chem. Soc., Chem. Commun. 1985;37 (q) Ref. 5o. (r) Ref. 5p.
64. For synthesis of prosopinine and/or desoxoprosopinine: (a) Ref. 5b. (b) Enders D., Kirchhoff J.H. Synthesis. 2000;2099 (c) Ref. 5e. (d) Agami C., County F., Lam H., Mathieu H. Tetrahedron. 54:1998;8783 (e) Agami C., County F., Mathieu H. Tetrahedron Lett. 39:1998;3505 (f) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron Lett. 38:1997;7469 (g) Ref. 5j. (h) Hirai Y., Watanabe J., Nozaki T., Yokoyama H., Yamaguchi S. J. Org. Chem. 62:1997;776 (i) Yuasa Y., Ando J., Shibuya S. J. Chem. Soc., Perkin Trans. 1. 1996;793 (j) Yuasa Y., Ando J., Shibuya S. Tetrahedron: Asymmetry. 6:1995;1525 (k) Ref. 5l. (l) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575 (m) Cook G.R., Beholz L.G., Stille J.R. Tetrahedron Lett. 35:1994;1669 (n) Ref. 5m. (o) Ciufolini M.A., Hermann C.W., Whitmire K.H., Byrne N.E. J. Am. Chem. Soc. 111:1989;3473 (p) Holmes A.B., Thompson J., Baxter A.J.G., Dixon J. J. Chem. Soc., Chem. Commun. 1985;37 (q) Ref. 5o. (r) Ref. 5p.
65. For synthesis of prosopinine and/or desoxoprosopinine: (a) Ref. 5b. (b) Enders D., Kirchhoff J.H. Synthesis. 2000;2099 (c) Ref. 5e. (d) Agami C., County F., Lam H., Mathieu H. Tetrahedron. 54:1998;8783 (e) Agami C., County F., Mathieu H. Tetrahedron Lett. 39:1998;3505 (f) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron Lett. 38:1997;7469 (g) Ref. 5j. (h) Hirai Y., Watanabe J., Nozaki T., Yokoyama H., Yamaguchi S. J. Org. Chem. 62:1997;776 (i) Yuasa Y., Ando J., Shibuya S. J. Chem. Soc., Perkin Trans. 1. 1996;793 (j) Yuasa Y., Ando J., Shibuya S. Tetrahedron: Asymmetry. 6:1995;1525 (k) Ref. 5l. (l) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575 (m) Cook G.R., Beholz L.G., Stille J.R. Tetrahedron Lett. 35:1994;1669 (n) Ref. 5m. (o) Ciufolini M.A., Hermann C.W., Whitmire K.H., Byrne N.E. J. Am. Chem. Soc. 111:1989;3473 (p) Holmes A.B., Thompson J., Baxter A.J.G., Dixon J. J. Chem. Soc., Chem. Commun. 1985;37 (q) Ref. 5o. (r) Ref. 5p.
66. For synthesis of prosopinine and/or desoxoprosopinine: (a) Ref. 5b. (b) Enders D., Kirchhoff J.H. Synthesis. 2000;2099 (c) Ref. 5e. (d) Agami C., County F., Lam H., Mathieu H. Tetrahedron. 54:1998;8783 (e) Agami C., County F., Mathieu H. Tetrahedron Lett. 39:1998;3505 (f) Kadota I., Kawada M., Muramatsu Y., Yamamoto Y. Tetrahedron Lett. 38:1997;7469 (g) Ref. 5j. (h) Hirai Y., Watanabe J., Nozaki T., Yokoyama H., Yamaguchi S. J. Org. Chem. 62:1997;776 (i) Yuasa Y., Ando J., Shibuya S. J. Chem. Soc., Perkin Trans. 1. 1996;793 (j) Yuasa Y., Ando J., Shibuya S. Tetrahedron: Asymmetry. 6:1995;1525 (k) Ref. 5l. (l) Cook G.R., Beholz L.G., Stille J.R. J. Org. Chem. 59:1994;3575 (m) Cook G.R., Beholz L.G., Stille J.R. Tetrahedron Lett. 35:1994;1669 (n) Ref. 5m. (o) Ciufolini M.A., Hermann C.W., Whitmire K.H., Byrne N.E. J. Am. Chem. Soc. 111:1989;3473 (p) Holmes A.B., Thompson J., Baxter A.J.G., Dixon J. J. Chem. Soc., Chem. Commun. 1985;37 (q) Ref. 5o. (r) Ref. 5p.
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93. 2; (iii) cat. DMAP, tolune, reflux ( 11:83%, 23:87%).