Facile transformation of 2-azetidinones to 2-piperidones: Application to the synthesis of the indolizidine skeleton and (8S,8aS)-perhydro-8-indolizinol

Journal of Organic Chemistry

Volumn 68, Issue 6, 2003, Pages 2471-2474

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

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

Author keywords

[No Author keywords available]

Indexed keywords

FACILE TRANSFORMATION;

CATALYST ACTIVITY; HYDROXYLATION; OLEFINS; RUTHENIUM; SYNTHESIS (CHEMICAL);

KETONES;

2 AZETIDINONE DERIVATIVE; 4 OLEFINIC 2 AZETIDINONE; 8 (BENZYLOXY) 3,5,6,7,8,8A HEXAHYDRO 5 INDOLIZIDINONE; 8 (BENZYLOXY) 3,5,8,8A TETRAHYDRO 5 INDOLIZIDINONE; 8,8A PERHYDRO 8 INDOLIZINOL; CARBON; DIOLEFINIC 2 PIPERIDONE; INDOLIZIDINE ALKALOID; LACTAM; PIPERIDONE DERIVATIVE; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHIRALITY; CRYSTAL STRUCTURE; HYDROXYLATION; RING CLOSING METATHESIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0037459751     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026817n     Document Type: Article

References (41)

1. For recent reviews of synthesis and biological activity, see: (a) Nemr, A. E. Tetrahedron 2000, 56, 8579. (b) Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645. (c) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. 1999, 38, 2300. (d) Michael, J. P. Nat. Prod. Rep. 1999, 16, 675. (e) Elbein, A. D.; Molyneux, R. J. In Iminosugars as Glycosidase Inhibitors; Stutz, A. E., Ed.; Wiley-VCH: Weinheim, Germany, 1999; p 216. (f) Michael, J. P. Nat. Prod. Rep. 1997, 14, 619. (g) Takahata, H.; Momose, T. In The Alkaloids; Cordell, G. A., Ed.; Academic: San Diego, CA, 1993; Vol. 44, Chapter 3. (h) Elbein, A. D.; Molyneux, R. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley and Sons: New York, 1987; Vol. 5
2. For recent reviews of synthesis and biological activity, see: (a) Nemr, A. E. Tetrahedron 2000, 56, 8579. (b) Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645. (c) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. 1999, 38, 2300. (d) Michael, J. P. Nat. Prod. Rep. 1999, 16, 675. (e) Elbein, A. D.; Molyneux, R. J. In Iminosugars as Glycosidase Inhibitors; Stutz, A. E., Ed.; Wiley-VCH: Weinheim, Germany, 1999; p 216. (f) Michael, J. P. Nat. Prod. Rep. 1997, 14, 619. (g) Takahata, H.; Momose, T. In The Alkaloids; Cordell, G. A., Ed.; Academic: San Diego, CA, 1993; Vol. 44, Chapter 3. (h) Elbein, A. D.; Molyneux, R. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley and Sons: New York, 1987; Vol. 5
3. For recent reviews of synthesis and biological activity, see: (a) Nemr, A. E. Tetrahedron 2000, 56, 8579. (b) Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645. (c) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. 1999, 38, 2300. (d) Michael, J. P. Nat. Prod. Rep. 1999, 16, 675. (e) Elbein, A. D.; Molyneux, R. J. In Iminosugars as Glycosidase Inhibitors; Stutz, A. E., Ed.; Wiley-VCH: Weinheim, Germany, 1999; p 216. (f) Michael, J. P. Nat. Prod. Rep. 1997, 14, 619. (g) Takahata, H.; Momose, T. In The Alkaloids; Cordell, G. A., Ed.; Academic: San Diego, CA, 1993; Vol. 44, Chapter 3. (h) Elbein, A. D.; Molyneux, R. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley and Sons: New York, 1987; Vol. 5
4. For recent reviews of synthesis and biological activity, see: (a) Nemr, A. E. Tetrahedron 2000, 56, 8579. (b) Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645. (c) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. 1999, 38, 2300. (d) Michael, J. P. Nat. Prod. Rep. 1999, 16, 675. (e) Elbein, A. D.; Molyneux, R. J. In Iminosugars as Glycosidase Inhibitors; Stutz, A. E., Ed.; Wiley-VCH: Weinheim, Germany, 1999; p 216. (f) Michael, J. P. Nat. Prod. Rep. 1997, 14, 619. (g) Takahata, H.; Momose, T. In The Alkaloids; Cordell, G. A., Ed.; Academic: San Diego, CA, 1993; Vol. 44, Chapter 3. (h) Elbein, A. D.; Molyneux, R. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley and Sons: New York, 1987; Vol. 5
5. For recent reviews of synthesis and biological activity, see: (a) Nemr, A. E. Tetrahedron 2000, 56, 8579. (b) Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645. (c) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. 1999, 38, 2300. (d) Michael, J. P. Nat. Prod. Rep. 1999, 16, 675. (e) Elbein, A. D.; Molyneux, R. J. In Iminosugars as Glycosidase Inhibitors; Stutz, A. E., Ed.; Wiley-VCH: Weinheim, Germany, 1999; p 216. (f) Michael, J. P. Nat. Prod. Rep. 1997, 14, 619. (g) Takahata, H.; Momose, T. In The Alkaloids; Cordell, G. A., Ed.; Academic: San Diego, CA, 1993; Vol. 44, Chapter 3. (h) Elbein, A. D.; Molyneux, R. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley and Sons: New York, 1987; Vol. 5.
6. For recent reviews of synthesis and biological activity, see: (a) Nemr, A. E. Tetrahedron 2000, 56, 8579. (b) Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645. (c) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. 1999, 38, 2300. (d) Michael, J. P. Nat. Prod. Rep. 1999, 16, 675. (e) Elbein, A. D.; Molyneux, R. J. In Iminosugars as Glycosidase Inhibitors; Stutz, A. E., Ed.; Wiley-VCH: Weinheim, Germany, 1999; p 216. (f) Michael, J. P. Nat. Prod. Rep. 1997, 14, 619. (g) Takahata, H.; Momose, T. In The Alkaloids; Cordell, G. A., Ed.; Academic: San Diego, CA, 1993; Vol. 44, Chapter 3. (h) Elbein, A. D.; Molyneux, R. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley and Sons: New York, 1987; Vol. 5.
7. For recent reviews of synthesis and biological activity, see: (a) Nemr, A. E. Tetrahedron 2000, 56, 8579. (b) Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645. (c) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. 1999, 38, 2300. (d) Michael, J. P. Nat. Prod. Rep. 1999, 16, 675. (e) Elbein, A. D.; Molyneux, R. J. In Iminosugars as Glycosidase Inhibitors; Stutz, A. E., Ed.; Wiley-VCH: Weinheim, Germany, 1999; p 216. (f) Michael, J. P. Nat. Prod. Rep. 1997, 14, 619. (g) Takahata, H.; Momose, T. In The Alkaloids; Cordell, G. A., Ed.; Academic: San Diego, CA, 1993; Vol. 44, Chapter 3. (h) Elbein, A. D.; Molyneux, R. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley and Sons: New York, 1987; Vol. 5.
8. For recent reviews of synthesis and biological activity, see: (a) Nemr, A. E. Tetrahedron 2000, 56, 8579. (b) Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645. (c) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. 1999, 38, 2300. (d) Michael, J. P. Nat. Prod. Rep. 1999, 16, 675. (e) Elbein, A. D.; Molyneux, R. J. In Iminosugars as Glycosidase Inhibitors; Stutz, A. E., Ed.; Wiley-VCH: Weinheim, Germany, 1999; p 216. (f) Michael, J. P. Nat. Prod. Rep. 1997, 14, 619. (g) Takahata, H.; Momose, T. In The Alkaloids; Cordell, G. A., Ed.; Academic: San Diego, CA, 1993; Vol. 44, Chapter 3. (h) Elbein, A. D.; Molyneux, R. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley and Sons: New York, 1987; Vol. 5.
9. For some representative examples of synthesis, see: (a) Paolucci, C.; Mattioli, L. J. Org. Chem. 2001, 66, 4787. (b) Park, S. O.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621. (c) Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971. (d) Sibi, M. P.; Christensen, J. W. J. Org. Chem. 1999, 64, 6434. (e) Yoda, H.; Kawauchi, M.; Takabe, K. Synlett 1998, 137. (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (g) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (h) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (i) Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (j) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (k) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358. (l) Jirousek, M. R.; Cheung, A. W.H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. W. Tetrahedron Lett. 1993, 34, 3671. (m) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397. (n) Chamberlin, A. R.; Miller, S. A. J. Am. Chem. Soc. 1990, 112, 8100. (o) Ikota, N.; Hanaki, A Chem. Pharm. Bull. 1990, 38, 2712. (p) Heitz, M.-P.; Overman, L. E. J. Org. Chem. 1989, 54, 2591. (q) Bennett, R. B., III; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580.
10. For some representative examples of synthesis, see: (a) Paolucci, C.; Mattioli, L. J. Org. Chem. 2001, 66, 4787. (b) Park, S. O.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621. (c) Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971. (d) Sibi, M. P.; Christensen, J. W. J. Org. Chem. 1999, 64, 6434. (e) Yoda, H.; Kawauchi, M.; Takabe, K. Synlett 1998, 137. (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (g) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (h) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (i) Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (j) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (k) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358. (l) Jirousek, M. R.; Cheung, A. W.H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. W. Tetrahedron Lett. 1993, 34, 3671. (m) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397. (n) Chamberlin, A. R.; Miller, S. A. J. Am. Chem. Soc. 1990, 112, 8100. (o) Ikota, N.; Hanaki, A Chem. Pharm. Bull. 1990, 38, 2712. (p) Heitz, M.-P.; Overman, L. E. J. Org. Chem. 1989, 54, 2591. (q) Bennett, R. B., III; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580.
11. For some representative examples of synthesis, see: (a) Paolucci, C.; Mattioli, L. J. Org. Chem. 2001, 66, 4787. (b) Park, S. O.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621. (c) Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971. (d) Sibi, M. P.; Christensen, J. W. J. Org. Chem. 1999, 64, 6434. (e) Yoda, H.; Kawauchi, M.; Takabe, K. Synlett 1998, 137. (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (g) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (h) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (i) Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (j) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (k) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358. (l) Jirousek, M. R.; Cheung, A. W.H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. W. Tetrahedron Lett. 1993, 34, 3671. (m) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397. (n) Chamberlin, A. R.; Miller, S. A. J. Am. Chem. Soc. 1990, 112, 8100. (o) Ikota, N.; Hanaki, A Chem. Pharm. Bull. 1990, 38, 2712. (p) Heitz, M.-P.; Overman, L. E. J. Org. Chem. 1989, 54, 2591. (q) Bennett, R. B., III; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580.
12. For some representative examples of synthesis, see: (a) Paolucci, C.; Mattioli, L. J. Org. Chem. 2001, 66, 4787. (b) Park, S. O.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621. (c) Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971. (d) Sibi, M. P.; Christensen, J. W. J. Org. Chem. 1999, 64, 6434. (e) Yoda, H.; Kawauchi, M.; Takabe, K. Synlett 1998, 137. (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (g) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (h) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (i) Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (j) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (k) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358. (l) Jirousek, M. R.; Cheung, A. W.H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. W. Tetrahedron Lett. 1993, 34, 3671. (m) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397. (n) Chamberlin, A. R.; Miller, S. A. J. Am. Chem. Soc. 1990, 112, 8100. (o) Ikota, N.; Hanaki, A Chem. Pharm. Bull. 1990, 38, 2712. (p) Heitz, M.-P.; Overman, L. E. J. Org. Chem. 1989, 54, 2591. (q) Bennett, R. B., III; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580.
13. For some representative examples of synthesis, see: (a) Paolucci, C.; Mattioli, L. J. Org. Chem. 2001, 66, 4787. (b) Park, S. O.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621. (c) Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971. (d) Sibi, M. P.; Christensen, J. W. J. Org. Chem. 1999, 64, 6434. (e) Yoda, H.; Kawauchi, M.; Takabe, K. Synlett 1998, 137. (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (g) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (h) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (i) Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (j) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (k) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358. (l) Jirousek, M. R.; Cheung, A. W.H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. W. Tetrahedron Lett. 1993, 34, 3671. (m) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397. (n) Chamberlin, A. R.; Miller, S. A. J. Am. Chem. Soc. 1990, 112, 8100. (o) Ikota, N.; Hanaki, A Chem. Pharm. Bull. 1990, 38, 2712. (p) Heitz, M.-P.; Overman, L. E. J. Org. Chem. 1989, 54, 2591. (q) Bennett, R. B., III; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580.
14. For some representative examples of synthesis, see: (a) Paolucci, C.; Mattioli, L. J. Org. Chem. 2001, 66, 4787. (b) Park, S. O.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621. (c) Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971. (d) Sibi, M. P.; Christensen, J. W. J. Org. Chem. 1999, 64, 6434. (e) Yoda, H.; Kawauchi, M.; Takabe, K. Synlett 1998, 137. (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (g) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (h) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (i) Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (j) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (k) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358. (l) Jirousek, M. R.; Cheung, A. W.H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. W. Tetrahedron Lett. 1993, 34, 3671. (m) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397. (n) Chamberlin, A. R.; Miller, S. A. J. Am. Chem. Soc. 1990, 112, 8100. (o) Ikota, N.; Hanaki, A Chem. Pharm. Bull. 1990, 38, 2712. (p) Heitz, M.-P.; Overman, L. E. J. Org. Chem. 1989, 54, 2591. (q) Bennett, R. B., III; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580.
15. For some representative examples of synthesis, see: (a) Paolucci, C.; Mattioli, L. J. Org. Chem. 2001, 66, 4787. (b) Park, S. O.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621. (c) Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971. (d) Sibi, M. P.; Christensen, J. W. J. Org. Chem. 1999, 64, 6434. (e) Yoda, H.; Kawauchi, M.; Takabe, K. Synlett 1998, 137. (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (g) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (h) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (i) Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (j) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (k) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358. (l) Jirousek, M. R.; Cheung, A. W.H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. W. Tetrahedron Lett. 1993, 34, 3671. (m) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397. (n) Chamberlin, A. R.; Miller, S. A. J. Am. Chem. Soc. 1990, 112, 8100. (o) Ikota, N.; Hanaki, A Chem. Pharm. Bull. 1990, 38, 2712. (p) Heitz, M.-P.; Overman, L. E. J. Org. Chem. 1989, 54, 2591. (q) Bennett, R. B., III; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580.
16. For some representative examples of synthesis, see: (a) Paolucci, C.; Mattioli, L. J. Org. Chem. 2001, 66, 4787. (b) Park, S. O.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621. (c) Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971. (d) Sibi, M. P.; Christensen, J. W. J. Org. Chem. 1999, 64, 6434. (e) Yoda, H.; Kawauchi, M.; Takabe, K. Synlett 1998, 137. (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (g) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (h) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (i) Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (j) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (k) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358. (l) Jirousek, M. R.; Cheung, A. W.H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. W. Tetrahedron Lett. 1993, 34, 3671. (m) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397. (n) Chamberlin, A. R.; Miller, S. A. J. Am. Chem. Soc. 1990, 112, 8100. (o) Ikota, N.; Hanaki, A Chem. Pharm. Bull. 1990, 38, 2712. (p) Heitz, M.-P.; Overman, L. E. J. Org. Chem. 1989, 54, 2591. (q) Bennett, R. B., III; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580.
17. For some representative examples of synthesis, see: (a) Paolucci, C.; Mattioli, L. J. Org. Chem. 2001, 66, 4787. (b) Park, S. O.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621. (c) Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971. (d) Sibi, M. P.; Christensen, J. W. J. Org. Chem. 1999, 64, 6434. (e) Yoda, H.; Kawauchi, M.; Takabe, K. Synlett 1998, 137. (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (g) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (h) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (i) Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (j) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (k) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358. (l) Jirousek, M. R.; Cheung, A. W.H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. W. Tetrahedron Lett. 1993, 34, 3671. (m) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397. (n) Chamberlin, A. R.; Miller, S. A. J. Am. Chem. Soc. 1990, 112, 8100. (o) Ikota, N.; Hanaki, A Chem. Pharm. Bull. 1990, 38, 2712. (p) Heitz, M.-P.; Overman, L. E. J. Org. Chem. 1989, 54, 2591. (q) Bennett, R. B., III; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580.
18. For some representative examples of synthesis, see: (a) Paolucci, C.; Mattioli, L. J. Org. Chem. 2001, 66, 4787. (b) Park, S. O.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621. (c) Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971. (d) Sibi, M. P.; Christensen, J. W. J. Org. Chem. 1999, 64, 6434. (e) Yoda, H.; Kawauchi, M.; Takabe, K. Synlett 1998, 137. (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (g) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (h) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (i) Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (j) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (k) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358. (l) Jirousek, M. R.; Cheung, A. W.H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. W. Tetrahedron Lett. 1993, 34, 3671. (m) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397. (n) Chamberlin, A. R.; Miller, S. A. J. Am. Chem. Soc. 1990, 112, 8100. (o) Ikota, N.; Hanaki, A Chem. Pharm. Bull. 1990, 38, 2712. (p) Heitz, M.-P.; Overman, L. E. J. Org. Chem. 1989, 54, 2591. (q) Bennett, R. B., III; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580.
19. For some representative examples of synthesis, see: (a) Paolucci, C.; Mattioli, L. J. Org. Chem. 2001, 66, 4787. (b) Park, S. O.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621. (c) Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971. (d) Sibi, M. P.; Christensen, J. W. J. Org. Chem. 1999, 64, 6434. (e) Yoda, H.; Kawauchi, M.; Takabe, K. Synlett 1998, 137. (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (g) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (h) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (i) Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (j) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (k) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358. (l) Jirousek, M. R.; Cheung, A. W.H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. W. Tetrahedron Lett. 1993, 34, 3671. (m) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397. (n) Chamberlin, A. R.; Miller, S. A. J. Am. Chem. Soc. 1990, 112, 8100. (o) Ikota, N.; Hanaki, A Chem. Pharm. Bull. 1990, 38, 2712. (p) Heitz, M.-P.; Overman, L. E. J. Org. Chem. 1989, 54, 2591. (q) Bennett, R. B., III; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580.
20. For some representative examples of synthesis, see: (a) Paolucci, C.; Mattioli, L. J. Org. Chem. 2001, 66, 4787. (b) Park, S. O.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621. (c) Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971. (d) Sibi, M. P.; Christensen, J. W. J. Org. Chem. 1999, 64, 6434. (e) Yoda, H.; Kawauchi, M.; Takabe, K. Synlett 1998, 137. (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (g) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (h) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (i) Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (j) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (k) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358. (l) Jirousek, M. R.; Cheung, A. W.H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. W. Tetrahedron Lett. 1993, 34, 3671. (m) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397. (n) Chamberlin, A. R.; Miller, S. A. J. Am. Chem. Soc. 1990, 112, 8100. (o) Ikota, N.; Hanaki, A Chem. Pharm. Bull. 1990, 38, 2712. (p) Heitz, M.-P.; Overman, L. E. J. Org. Chem. 1989, 54, 2591. (q) Bennett, R. B., III; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580.
21. For some representative examples of synthesis, see: (a) Paolucci, C.; Mattioli, L. J. Org. Chem. 2001, 66, 4787. (b) Park, S. O.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621. (c) Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971. (d) Sibi, M. P.; Christensen, J. W. J. Org. Chem. 1999, 64, 6434. (e) Yoda, H.; Kawauchi, M.; Takabe, K. Synlett 1998, 137. (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (g) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (h) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (i) Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (j) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (k) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358. (l) Jirousek, M. R.; Cheung, A. W.H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. W. Tetrahedron Lett. 1993, 34, 3671. (m) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397. (n) Chamberlin, A. R.; Miller, S. A. J. Am. Chem. Soc. 1990, 112, 8100. (o) Ikota, N.; Hanaki, A Chem. Pharm. Bull. 1990, 38, 2712. (p) Heitz, M.-P.; Overman, L. E. J. Org. Chem. 1989, 54, 2591. (q) Bennett, R. B., III; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580.
22. For some representative examples of synthesis, see: (a) Paolucci, C.; Mattioli, L. J. Org. Chem. 2001, 66, 4787. (b) Park, S. O.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621. (c) Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971. (d) Sibi, M. P.; Christensen, J. W. J. Org. Chem. 1999, 64, 6434. (e) Yoda, H.; Kawauchi, M.; Takabe, K. Synlett 1998, 137. (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (g) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (h) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (i) Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (j) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (k) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358. (l) Jirousek, M. R.; Cheung, A. W.H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. W. Tetrahedron Lett. 1993, 34, 3671. (m) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397. (n) Chamberlin, A. R.; Miller, S. A. J. Am. Chem. Soc. 1990, 112, 8100. (o) Ikota, N.; Hanaki, A Chem. Pharm. Bull. 1990, 38, 2712. (p) Heitz, M.-P.; Overman, L. E. J. Org. Chem. 1989, 54, 2591. (q) Bennett, R. B., III; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580.
23. For some representative examples of synthesis, see: (a) Paolucci, C.; Mattioli, L. J. Org. Chem. 2001, 66, 4787. (b) Park, S. O.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621. (c) Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971. (d) Sibi, M. P.; Christensen, J. W. J. Org. Chem. 1999, 64, 6434. (e) Yoda, H.; Kawauchi, M.; Takabe, K. Synlett 1998, 137. (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (g) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (h) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (i) Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (j) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (k) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358. (l) Jirousek, M. R.; Cheung, A. W.H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. W. Tetrahedron Lett. 1993, 34, 3671. (m) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397. (n) Chamberlin, A. R.; Miller, S. A. J. Am. Chem. Soc. 1990, 112, 8100. (o) Ikota, N.; Hanaki, A Chem. Pharm. Bull. 1990, 38, 2712. (p) Heitz, M.-P.; Overman, L. E. J. Org. Chem. 1989, 54, 2591. (q) Bennett, R. B., III; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580.
24. For some representative examples of synthesis, see: (a) Paolucci, C.; Mattioli, L. J. Org. Chem. 2001, 66, 4787. (b) Park, S. O.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621. (c) Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971. (d) Sibi, M. P.; Christensen, J. W. J. Org. Chem. 1999, 64, 6434. (e) Yoda, H.; Kawauchi, M.; Takabe, K. Synlett 1998, 137. (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (g) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (h) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (i) Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (j) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (k) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358. (l) Jirousek, M. R.; Cheung, A. W.H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. W. Tetrahedron Lett. 1993, 34, 3671. (m) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397. (n) Chamberlin, A. R.; Miller, S. A. J. Am. Chem. Soc. 1990, 112, 8100. (o) Ikota, N.; Hanaki, A Chem. Pharm. Bull. 1990, 38, 2712. (p) Heitz, M.-P.; Overman, L. E. J. Org. Chem. 1989, 54, 2591. (q) Bennett, R. B., III; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580.
25. For some representative examples of synthesis, see: (a) Paolucci, C.; Mattioli, L. J. Org. Chem. 2001, 66, 4787. (b) Park, S. O.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621. (c) Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971. (d) Sibi, M. P.; Christensen, J. W. J. Org. Chem. 1999, 64, 6434. (e) Yoda, H.; Kawauchi, M.; Takabe, K. Synlett 1998, 137. (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217. (g) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761. (h) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (i) Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049. (j) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. (k) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358. (l) Jirousek, M. R.; Cheung, A. W.H.; Babine, R. E.; Sass, P. M.; Schow, S. R.; Wick, M. W. Tetrahedron Lett. 1993, 34, 3671. (m) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397. (n) Chamberlin, A. R.; Miller, S. A. J. Am. Chem. Soc. 1990, 112, 8100. (o) Ikota, N.; Hanaki, A Chem. Pharm. Bull. 1990, 38, 2712. (p) Heitz, M.-P.; Overman, L. E. J. Org. Chem. 1989, 54, 2591. (q) Bennett, R. B., III; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580.
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