Enantioselective synthesis of paraconic acids

Chemistry - A European Journal

Volumn 9, Issue 1, 2003, Pages 260-270

  Chhor, Rakeshwar B ^a   Nosse, Bernd ^a   Sörgel, Sebastian ^a   Böhm, Claudius ^a   Seitz, Michael ^a   Reiser, Oliver ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Asymmetric synthesis; Lactones; Metathesis; Natural products; Total synthesis

Indexed keywords

ANTIBIOTICS; CATALYSIS; CHEMOTHERAPY; COPPER; RUTHENIUM; STEREOCHEMISTRY;

METATHESIS REACTIONS;

ORGANIC ACIDS;

COPPER; GAMMA BUTYROLACTONE DERIVATIVE; METHYLENOLACTOCIN; NEPHROSTERANIC ACID; PARACONIC ACID; PROTOLICHESTERINIC ACID; PROTOPRAESOREDIOSIC ACID; ROCCELLARIC ACID; RUTHENIUM; UNCLASSIFIED DRUG;

ALLYLATION; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0037415070     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200390019     Document Type: Article

References (111)

1. a) H. M. R. Hoffmann, J. Rabe, Angew. Chem. 1985, 97, 96-112; Angew. Chem. Int. Ed. Engl. 1985, 24, 94-110;
2. a) H. M. R. Hoffmann, J. Rabe, Angew. Chem. 1985, 97, 96-112; Angew. Chem. Int. Ed. Engl. 1985, 24, 94-110;
3. b) S. S. C. Koch, A. R. Chamberlin, Studies in Natural Products Chemistry, Vol, 16 (Ed.: Atta-ur-Rahman), Elsevier. 1995, pp. 687-725.
4. a) D. Hoppe, Angew. Chem. 1984, 96, 930-946; Angew. Chem. Int. Ed. Engl. 1984, 23, 932-948;
5. a) D. Hoppe, Angew. Chem. 1984, 96, 930-946; Angew. Chem. Int. Ed. Engl. 1984, 23, 932-948;
6. b) H. Roder, G. Helmchen, E. M. Peters, K. Peters, H. G. v. Schnering, Angew. Chem. 1984, 96, 895-896; Angew. Chem. Int. Ed. Engl. 1984, 23, 898-899;
7. b) H. Roder, G. Helmchen, E. M. Peters, K. Peters, H. G. v. Schnering, Angew. Chem. 1984, 96, 895-896; Angew. Chem. Int. Ed. Engl. 1984, 23, 898-899;
8. c) D. Hoppe, O. Zschage, Angew. Chem. 1989, 101, 67-69; Angew. Chem. Int. Ed. Engl. 1989, 28, 69-71;
9. c) D. Hoppe, O. Zschage, Angew. Chem. 1989, 101, 67-69; Angew. Chem. Int. Ed. Engl. 1989, 28, 69-71;
10. d) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376-2410; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282-2316;
11. d) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376-2410; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282-2316;
12. e) H. Ahlbrecht, U. Beyer, Synthesis 1999, 365-390;
13. f) M. C. Whisler, L. Vaillancourt, P. Beak, Org. Lett. 2000, 2, 2655-2658;
14. g) T. A. Johnson, M. D. Curtis, P. Beak. J. Am. Chem. Soc. 2001, 123, 1004;
15. h) S. H. Lim, M. D. Curtis, P. Beak, Org. Lett. 2001, 3, 711-714;
16. i) A. Schlapbach, R. W. Hoffmann, Eur. J. Org. Chem. 2001, 323-328;
17. j) C. Gaul, D. Seebach, Helv. Chim. Acta 2002, 85, 963-978 and references therein;
18. k) M. Özlügedik, J. Kristensen, B. Wibbeling, R. Fröhlich, D. Hoppe, Eur. J. Org. Chem. 2002, 414-427 and references therein.
19. Review: M. Braun. Adv. Carbanion Chem. 1992, 1, 177-247.
20. Recent developments: a) V. Blandin, J.-F. Carpentier, A. Mortreux, Eur. J. Org. Chem. 1999, 1787-1793;
21. b) Q. Zhang, X. Lu, J. Am. Chem. Soc. 2000, 122, 7604-7605;
22. c) Y. Caro, F. Masaguer, E. Ravina, Tetrahedron: Asymmetry 2001, 12, 1723-1726;
23. d) S. K. Mandal, S. R. Amin, W. E. Crowe, J. Am. Chem. Soc. 2001, 123, 6457-6458;
24. e) D. J. Spielvogel, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 3500-3501;
25. f) M. P. Doyle, W. Hu, M. V. Valenzuela, J. Org. Chem. 2002, 67, 2954-2959.
26. a) H. Miyabe, K. Fujii, T. Goto, T. Naito, Org. Lett. 2000, 2, 4071-4074;
27. b) A.-M. Fernandez, J.-C. Plaquevent, L. Duhamel, J. Org. Chem. 1997, 62, 4007-4014;
28. c) M. P. Sibi, J. Lu, C. L. Talbacka, J. Org. Chem. 1996, 61, 7848-7855;
29. d) Z.-H. Peng, K. A. Woerpel, Org. Lett. 2001, 3, 675-678.
30. a) M. S. Maier, D. I. G. Marimon, C. A. Stortz, M. T. Adler, J. Nat. Prod. 1999, 62, 1565-1567;
31. b) B. K. Park, M. Nakagawa, A. Hirota, M. Nakayama, J. Antibiot. 1988, 41, 751-758.
32. a) T.-P. Loh, P.-L. Lye, Tetrahedron Lett. 2001, 41, 561-565;
33. b) P. K. Mandal, S. C. Roy, Tetrahedron 1999, 55, 11395-11398;
34. c) J. Lertvorachon, P. Meepowpan, Y. Thebtaranonth, Tetrahedron 1998, 54, 14341-14358;
35. d) P. K. Mandal, G. Maiti, S. C. Roy, J. Org. Chem. 1998, 63, 2829-2834;
36. e) A. Ghatak, S. Sarkar, S. Ghosh, Tetrahedron 1997, 53, 17335-17342;
37. f) R. E. Damon, R. H. Schlessinger, Tetrahedron Lett. 1976, 1561-1564;
38. g) R. M. Carlson, A. R. Oyler, J. Org. Chem. 1976, 41, 4065-4069;
39. h) J. Martin, P. C. Watts, F. Johnson, J. Org. Chem. 1974, 39, 1676-1681;
40. i) A. Löffler. R. D. Pratt, J. Pucknat, G. Gelbard. A.S. Dreiding, Chimica 1969, 23, 413-416;
41. j) E. E. van Tamelen, S. R. Bach, J. Am. Chem. Soc. 1958, 80, 3079-3086.
42. a) Y. Masaki, H. Arasaki, A. Itoh, Tetrahedron Lett. 1999, 40, 4829-4832;
43. b) J. Mulzer, N. Salimi, H. Hartl, Tetrahedron: Asymmetry 1993, 4, 457-471.
44. a) M. Bella, R. Margarita, C. Orlando, M. Orsini, L. Parlanti, G. Piancatelli, Tetrahedron Lett. 2000, 41, 561-565;
45. b) M. P. Sibi, J. Ji, Angew. Chem. 1997, 109, 266-268; Angew. Chem. Int. Ed, Engl. 1997, 36, 274-276;
46. b) M. P. Sibi, J. Ji, Angew. Chem. 1997, 109, 266-268; Angew. Chem. Int. Ed, Engl. 1997, 36, 274-276;
47. c) M. P. Sibi, P. K. Deshpande, A. J. L. Loggia, Synlett 1996, 343-345;
48. d) M. M. Murta, M. B. M. de Azevedo, A. E. Greene, J. Org. Chem. 1993. 58, 7537-7541;
49. e) M. B. M. de Azevedo, M. M. Murta, A. E. Greene, J. Org. Chem. 1992, 57, 4567-4569;
50. f) J. Mulzer, L. Kattner, A. R. Strecker, C. Schröder, J. Buschmann, C. Lehmann, P. Luger, J. Am. Chem. Soc. 1991, 113, 4218-4229.
51. a) M. Chandrasekharam, R.-S. Liu, J. Org. Chem. 1998, 63, 9122-9124;
52. b) X. Ariza, J. Garcia, M. Lopez, L. Montserrat, Synlett 2001, 120-122;
53. c) A. Vaupel, P. Knochel, J. Org. Chem. 1996. 61, 5743-5753;
54. d) T. Martin, C. M. Rodriguez, V. S. Martin, J. Org. Chem. 1996, 61, 6450-6453;
55. e) H. Takahata, Y. Uchida, T. Momose, J. Org. Chem, 1995, 60, 5628-5633;
56. f) G. Zhu, X. Lu, J. Org. Chem. 1995, 60, 1087-1089.
57. For an initial report on the synthesis of (-)-roccellaric acid using the strategy described here see: C. Böhm, O. Reiser, Org. Lett. 2001, 3, 1315.
58. Review: H.-U. Reißig, Top. Curr. Chem. 1988, 144, 73-135;
59. recent examples: a) A. Ullmann, M. Gruner, H.-U. Reißig, Chem. Eur. J. 1999, 5, 187-197;
60. P. K. Patra, H.-U. Reißig, Eur. J. Org. Chem. 2001, 4195-4206.
61. C. Brückner, H.-U. Reißig, J. Org. Chem. 1988, 53, 2440-2450.
62. a) E. Wenkert, M. Guo, R. Lavilla, B. Porter, K. Ramachandran, J.-H. Shue, J. Org. Chem. 1990, 55, 6203;
63. b) E. Wenkert, H. Khatuya, P. S. Klein, Tetrahedron Lett. 1999. 40, 5171-5174;
64. c) E. Wenkert. H. Khatuya, Tetrahedron Lett. 1999, 40, 5439-5442;
65. d) H. M. L. Davies, R.L. Calvo. Tetrahedron Lett. 1997, 38. 5623-5626;
66. e) H. M. L. Davies, R. Calvo, G. Ahmed, Tetrahedron Lett. 1997, 38, 1737-1740;
67. f) M. P. Doyle, B. J. Chapman. W. Hu, C. F. Garcia, Org. Lett. 1999, 1, 1327-1329;
68. g) P. C. Shieh. C. W. Ong, Tetrahedron 2001, 57, 7303-7307;
69. h) G. Maas, in Methoden der Organischen Chemie (Houben-Weyl), Vol. E17a (Ed.: A. deMeijere), Thieme, Stuttgart, 1996, p. 110-112 and 405-515.
70. a) E. Müller, H. Fricke, H. Kessler, Tetrahedron Lett. 1963, 1501-1503;
71. b) E. Müller, H. Kessler, Tetrahedron Lett. 1963, 1047- 1049.
72. D. A. Evans, K. A. Woerpel, M. M. Hinman, M. M. Faul, J. Am. Chem. Soc. 1991, 113, 726-728; for a review see: A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1-45.
73. D. A. Evans, K. A. Woerpel, M. M. Hinman, M. M. Faul, J. Am. Chem. Soc. 1991, 113, 726-728; for a review see: A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1-45.
74. O. Temme, S.-A. Taj, P. G. Andersson, J. Org. Chem. 1998, 63, 6007-6015.
75. See ref. [14e].
76. Preparation of 9a: M. Schinnerl, M. Seitz, A. Kaiser, O. Reiser, Org. Lett. 2001, 3, 4259-4262; preparation of 9b: D.A. Evans, G.S. Peterson, D. M. Barnes, K. R. Campos, K. A. Woerpel, J. Org. Chem. 1998. 63. 4541-4544; preparation of 9c according to the procedure described for 9b.
77. Preparation of 9a: M. Schinnerl, M. Seitz, A. Kaiser, O. Reiser, Org. Lett. 2001, 3, 4259-4262; preparation of 9b: D.A. Evans, G.S. Peterson, D. M. Barnes, K. R. Campos, K. A. Woerpel, J. Org. Chem. 1998. 63. 4541-4544; preparation of 9c according to the procedure described for 9b.
78. M. Glos, O. Reiser, Org. Lett. 2000, 2, 2045-2048.
79. For the preparation of tert-butyl diazoacetate see: a) H. G. von Schnering, Liebigs Ann. Chem, 1992, 1259-1269; (b) H. Lëdon, Synthesis 1974, 347-348.
80. For the preparation of tert-butyl diazoacetate see: a) H. G. von Schnering, Liebigs Ann. Chem, 1992, 1259-1269; (b) H. Lëdon, Synthesis 1974, 347-348.
81. For the preparation of ethyl diazoacetate see: F. Tietze, Reaction and Synthesis 1991, Thieme, 2nd ed., p. 135.
82. X-ray data for 8c-Et (CCDC-139843) can be obtained free of charge via www.ccdc.cam.ac.uk (or from the Cambridge Crystallographic Data in the X-ray studies [Flack parameter: 0,0(2)].
83. Review: A. Mengel, O. Reiser, Chem. Rev. 1999, 99, 1191-1223.
84. C. Boehm, M. Schinnerl, C. Bubert, M. Zabel, T. Labahn, O. Reiser, Eur. J. Org. Chem. 2000, 2955-2965.
85. a) J. Otera, N. Dan-oh, H. Nozaki, Tetrahedron 1992, 48, 1449-1456;
86. b) J. Otera, N. Dan-oh. H. Nozaki, J. Org. Chem. 1991, 56, 5307-5314;
87. c) R. Okawara, M. Wada, Adv. Organomet. Chem. 1967, 5, 137-167.
88. Using our strategy, the naturally occuring paraconic acids can also be synthesized starting from (ent)-5a/b and (ent)-6a readily available from (ent)-8c (cf. Table 1, entry 8).
89. E. Dalcanale, E Montanari, J. Org. Chem. 1986, 51, 567-69; for a review see: A. Raach, O. Reiser, J. Prakt. Chem. 2000, 605-608.
90. E. Dalcanale, E Montanari, J. Org. Chem. 1986, 51, 567-69; for a review see: A. Raach, O. Reiser, J. Prakt. Chem. 2000, 605-608.
91. a) T. M. Trnka, R.H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29;
92. b) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450;
93. c) A. Fürstner, O. R. Thiel, L. Ackermann, H.-J. Schanz, S. P. Nolan, J. Org. Chem. 2000, 65, 2204-2207.
94. a) S. Randl, S. Gessler, H. Wakamatsu, S. Blechert, Synlett 2001, 430-432;
95. b) A. K. Chatterjee, J. P. Morgan, M. Scholl, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 3783-3784
96. c) O. Brümmer, A. Rückert, S. Blechert, Chem. Eur. J. 1997, 3, 441-446.
97. CCDC-165928 (26).
98. A. K. Chatterjee, R. H. Grubbs, Org. Lett. 1999, 1, 1751-1753.
99. Stiles reagent: a) see ref. [9d]; b) J. Martin, P. C. Watts, F. Johnson, J. Org. Chem. 1974, 39, 1676-1681; c) L. A. Paquette, G. D. Annis, H. Schostarez, J. Am. Chem. Soc. 1982, 104, 6646-6653; Eschenmoser salt; d) H. Mattes, K. Hamada, C. Benezra, J. Med. Chem. 1987, 30, 1948-1951; e) I. Marcos, E. Redero, F. Bermejo, Tetrahedron Lett. 2000, 41, 8451-8455; base-mediated addition of formaldehyde followed by elimination; f) P. Klein, W. L. Nelson, J. Med. Chem. 1991, 34, 2438-2444; g) M. Tada, H. Yamada, A. Kanamori, K. Chiba, J Chem. Soc. Perkin Trans. 1 1993, 239-247; h) M. Schwaebe, R. D. Little, J. Org. Chem. 1996, 61, 3240-3244; i) L. A. Paquette, C. F. Sturino, X. Wang, J. C. Prodoger, D. Koh, J. Am. Chem. Soc. 1996, 118, 5620-5633; other methods; j) E. Krawczyk, A. Skowronska, Heteroat. Chem. 2000, 11, 353-361; reviews; k) P. A. Grieco, Synthesis 1975, 67-82; l) N. Petragnani, H. M. C. Ferraz, G. V. J. Silva, Synthesis 1986, 157-183.
100. Stiles reagent: a) see ref. [9d]; b) J. Martin, P. C. Watts, F. Johnson, J. Org. Chem. 1974, 39, 1676-1681; c) L. A. Paquette, G. D. Annis, H. Schostarez, J. Am. Chem. Soc. 1982, 104, 6646-6653; Eschenmoser salt; d) H. Mattes, K. Hamada, C. Benezra, J. Med. Chem. 1987, 30, 1948-1951; e) I. Marcos, E. Redero, F. Bermejo, Tetrahedron Lett. 2000, 41, 8451-8455; base-mediated addition of formaldehyde followed by elimination; f) P. Klein, W. L. Nelson, J. Med. Chem. 1991, 34, 2438-2444; g) M. Tada, H. Yamada, A. Kanamori, K. Chiba, J Chem. Soc. Perkin Trans. 1 1993, 239-247; h) M. Schwaebe, R. D. Little, J. Org. Chem. 1996, 61, 3240-3244; i) L. A. Paquette, C. F. Sturino, X. Wang, J. C. Prodoger, D. Koh, J. Am. Chem. Soc. 1996, 118, 5620-5633; other methods; j) E. Krawczyk, A. Skowronska, Heteroat. Chem. 2000, 11, 353-361; reviews; k) P. A. Grieco, Synthesis 1975, 67-82; l) N. Petragnani, H. M. C. Ferraz, G. V. J. Silva, Synthesis 1986, 157-183.
101. Stiles reagent: a) see ref. [9d]; b) J. Martin, P. C. Watts, F. Johnson, J. Org. Chem. 1974, 39, 1676-1681; c) L. A. Paquette, G. D. Annis, H. Schostarez, J. Am. Chem. Soc. 1982, 104, 6646-6653; Eschenmoser salt; d) H. Mattes, K. Hamada, C. Benezra, J. Med. Chem. 1987, 30, 1948-1951; e) I. Marcos, E. Redero, F. Bermejo, Tetrahedron Lett. 2000, 41, 8451-8455; base-mediated addition of formaldehyde followed by elimination; f) P. Klein, W. L. Nelson, J. Med. Chem. 1991, 34, 2438-2444; g) M. Tada, H. Yamada, A. Kanamori, K. Chiba, J Chem. Soc. Perkin Trans. 1 1993, 239-247; h) M. Schwaebe, R. D. Little, J. Org. Chem. 1996, 61, 3240-3244; i) L. A. Paquette, C. F. Sturino, X. Wang, J. C. Prodoger, D. Koh, J. Am. Chem. Soc. 1996, 118, 5620-5633; other methods; j) E. Krawczyk, A. Skowronska, Heteroat. Chem. 2000, 11, 353-361; reviews; k) P. A. Grieco, Synthesis 1975, 67-82; l) N. Petragnani, H. M. C. Ferraz, G. V. J. Silva, Synthesis 1986, 157-183.
102. Stiles reagent: a) see ref. [9d]; b) J. Martin, P. C. Watts, F. Johnson, J. Org. Chem. 1974, 39, 1676-1681; c) L. A. Paquette, G. D. Annis, H. Schostarez, J. Am. Chem. Soc. 1982, 104, 6646-6653; Eschenmoser salt; d) H. Mattes, K. Hamada, C. Benezra, J. Med. Chem. 1987, 30, 1948-1951; e) I. Marcos, E. Redero, F. Bermejo, Tetrahedron Lett. 2000, 41, 8451-8455; base-mediated addition of formaldehyde followed by elimination; f) P. Klein, W. L. Nelson, J. Med. Chem. 1991, 34, 2438-2444; g) M. Tada, H. Yamada, A. Kanamori, K. Chiba, J Chem. Soc. Perkin Trans. 1 1993, 239-247; h) M. Schwaebe, R. D. Little, J. Org. Chem. 1996, 61, 3240-3244; i) L. A. Paquette, C. F. Sturino, X. Wang, J. C. Prodoger, D. Koh, J. Am. Chem. Soc. 1996, 118, 5620-5633; other methods; j) E. Krawczyk, A. Skowronska, Heteroat. Chem. 2000, 11, 353-361; reviews; k) P. A. Grieco, Synthesis 1975, 67-82; l) N. Petragnani, H. M. C. Ferraz, G. V. J. Silva, Synthesis 1986, 157-183.
103. Stiles reagent: a) see ref. [9d]; b) J. Martin, P. C. Watts, F. Johnson, J. Org. Chem. 1974, 39, 1676-1681; c) L. A. Paquette, G. D. Annis, H. Schostarez, J. Am. Chem. Soc. 1982, 104, 6646-6653; Eschenmoser salt; d) H. Mattes, K. Hamada, C. Benezra, J. Med. Chem. 1987, 30, 1948-1951; e) I. Marcos, E. Redero, F. Bermejo, Tetrahedron Lett. 2000, 41, 8451-8455; base-mediated addition of formaldehyde followed by elimination; f) P. Klein, W. L. Nelson, J. Med. Chem. 1991, 34, 2438-2444; g) M. Tada, H. Yamada, A. Kanamori, K. Chiba, J Chem. Soc. Perkin Trans. 1 1993, 239-247; h) M. Schwaebe, R. D. Little, J. Org. Chem. 1996, 61, 3240-3244; i) L. A. Paquette, C. F. Sturino, X. Wang, J. C. Prodoger, D. Koh, J. Am. Chem. Soc. 1996, 118, 5620-5633; other methods; j) E. Krawczyk, A. Skowronska, Heteroat. Chem. 2000, 11, 353-361; reviews; k) P. A. Grieco, Synthesis 1975, 67-82; l) N. Petragnani, H. M. C. Ferraz, G. V. J. Silva, Synthesis 1986, 157-183.
104. Stiles reagent: a) see ref. [9d]; b) J. Martin, P. C. Watts, F. Johnson, J. Org. Chem. 1974, 39, 1676-1681; c) L. A. Paquette, G. D. Annis, H. Schostarez, J. Am. Chem. Soc. 1982, 104, 6646-6653; Eschenmoser salt; d) H. Mattes, K. Hamada, C. Benezra, J. Med. Chem. 1987, 30, 1948-1951; e) I. Marcos, E. Redero, F. Bermejo, Tetrahedron Lett. 2000, 41, 8451-8455; base-mediated addition of formaldehyde followed by elimination; f) P. Klein, W. L. Nelson, J. Med. Chem. 1991, 34, 2438-2444; g) M. Tada, H. Yamada, A. Kanamori, K. Chiba, J Chem. Soc. Perkin Trans. 1 1993, 239-247; h) M. Schwaebe, R. D. Little, J. Org. Chem. 1996, 61, 3240-3244; i) L. A. Paquette, C. F. Sturino, X. Wang, J. C. Prodoger, D. Koh, J. Am. Chem. Soc. 1996, 118, 5620-5633; other methods; j) E. Krawczyk, A. Skowronska, Heteroat. Chem. 2000, 11, 353-361; reviews; k) P. A. Grieco, Synthesis 1975, 67-82; l) N. Petragnani, H. M. C. Ferraz, G. V. J. Silva, Synthesis 1986, 157-183.
105. Stiles reagent: a) see ref. [9d]; b) J. Martin, P. C. Watts, F. Johnson, J. Org. Chem. 1974, 39, 1676-1681; c) L. A. Paquette, G. D. Annis, H. Schostarez, J. Am. Chem. Soc. 1982, 104, 6646-6653; Eschenmoser salt; d) H. Mattes, K. Hamada, C. Benezra, J. Med. Chem. 1987, 30, 1948-1951; e) I. Marcos, E. Redero, F. Bermejo, Tetrahedron Lett. 2000, 41, 8451-8455; base-mediated addition of formaldehyde followed by elimination; f) P. Klein, W. L. Nelson, J. Med. Chem. 1991, 34, 2438-2444; g) M. Tada, H. Yamada, A. Kanamori, K. Chiba, J Chem. Soc. Perkin Trans. 1 1993, 239-247; h) M. Schwaebe, R. D. Little, J. Org. Chem. 1996, 61, 3240-3244; i) L. A. Paquette, C. F. Sturino, X. Wang, J. C. Prodoger, D. Koh, J. Am. Chem. Soc. 1996, 118, 5620-5633; other methods; j) E. Krawczyk, A. Skowronska, Heteroat. Chem. 2000, 11, 353-361; reviews; k) P. A. Grieco, Synthesis 1975, 67-82; l) N. Petragnani, H. M. C. Ferraz, G. V. J. Silva, Synthesis 1986, 157-183.
106. Stiles reagent: a) see ref. [9d]; b) J. Martin, P. C. Watts, F. Johnson, J. Org. Chem. 1974, 39, 1676-1681; c) L. A. Paquette, G. D. Annis, H. Schostarez, J. Am. Chem. Soc. 1982, 104, 6646-6653; Eschenmoser salt; d) H. Mattes, K. Hamada, C. Benezra, J. Med. Chem. 1987, 30, 1948-1951; e) I. Marcos, E. Redero, F. Bermejo, Tetrahedron Lett. 2000, 41, 8451-8455; base-mediated addition of formaldehyde followed by elimination; f) P. Klein, W. L. Nelson, J. Med. Chem. 1991, 34, 2438-2444; g) M. Tada, H. Yamada, A. Kanamori, K. Chiba, J Chem. Soc. Perkin Trans. 1 1993, 239-247; h) M. Schwaebe, R. D. Little, J. Org. Chem. 1996, 61, 3240-3244; i) L. A. Paquette, C. F. Sturino, X. Wang, J. C. Prodoger, D. Koh, J. Am. Chem. Soc. 1996, 118, 5620-5633; other methods; j) E. Krawczyk, A. Skowronska, Heteroat. Chem. 2000, 11, 353-361; reviews; k) P. A. Grieco, Synthesis 1975, 67-82; l) N. Petragnani, H. M. C. Ferraz, G. V. J. Silva, Synthesis 1986, 157-183.
107. Stiles reagent: a) see ref. [9d]; b) J. Martin, P. C. Watts, F. Johnson, J. Org. Chem. 1974, 39, 1676-1681; c) L. A. Paquette, G. D. Annis, H. Schostarez, J. Am. Chem. Soc. 1982, 104, 6646-6653; Eschenmoser salt; d) H. Mattes, K. Hamada, C. Benezra, J. Med. Chem. 1987, 30, 1948-1951; e) I. Marcos, E. Redero, F. Bermejo, Tetrahedron Lett. 2000, 41, 8451-8455; base-mediated addition of formaldehyde followed by elimination; f) P. Klein, W. L. Nelson, J. Med. Chem. 1991, 34, 2438-2444; g) M. Tada, H. Yamada, A. Kanamori, K. Chiba, J Chem. Soc. Perkin Trans. 1 1993, 239-247; h) M. Schwaebe, R. D. Little, J. Org. Chem. 1996, 61, 3240-3244; i) L. A. Paquette, C. F. Sturino, X. Wang, J. C. Prodoger, D. Koh, J. Am. Chem. Soc. 1996, 118, 5620-5633; other methods; j) E. Krawczyk, A. Skowronska, Heteroat. Chem. 2000, 11, 353-361; reviews; k) P. A. Grieco, Synthesis 1975, 67-82; l) N. Petragnani, H. M. C. Ferraz, G. V. J. Silva, Synthesis 1986, 157-183.
108. Stiles reagent: a) see ref. [9d]; b) J. Martin, P. C. Watts, F. Johnson, J. Org. Chem. 1974, 39, 1676-1681; c) L. A. Paquette, G. D. Annis, H. Schostarez, J. Am. Chem. Soc. 1982, 104, 6646-6653; Eschenmoser salt; d) H. Mattes, K. Hamada, C. Benezra, J. Med. Chem. 1987, 30, 1948-1951; e) I. Marcos, E. Redero, F. Bermejo, Tetrahedron Lett. 2000, 41, 8451-8455; base-mediated addition of formaldehyde followed by elimination; f) P. Klein, W. L. Nelson, J. Med. Chem. 1991, 34, 2438-2444; g) M. Tada, H. Yamada, A. Kanamori, K. Chiba, J Chem. Soc. Perkin Trans. 1 1993, 239-247; h) M. Schwaebe, R. D. Little, J. Org. Chem. 1996, 61, 3240-3244; i) L. A. Paquette, C. F. Sturino, X. Wang, J. C. Prodoger, D. Koh, J. Am. Chem. Soc. 1996, 118, 5620-5633; other methods; j) E. Krawczyk, A. Skowronska, Heteroat. Chem. 2000, 11, 353-361; reviews; k) P. A. Grieco, Synthesis 1975, 67-82; l) N. Petragnani, H. M. C. Ferraz, G. V. J. Silva, Synthesis 1986, 157-183.
109. Stiles reagent: a) see ref. [9d]; b) J. Martin, P. C. Watts, F. Johnson, J. Org. Chem. 1974, 39, 1676-1681; c) L. A. Paquette, G. D. Annis, H. Schostarez, J. Am. Chem. Soc. 1982, 104, 6646-6653; Eschenmoser salt; d) H. Mattes, K. Hamada, C. Benezra, J. Med. Chem. 1987, 30, 1948-1951; e) I. Marcos, E. Redero, F. Bermejo, Tetrahedron Lett. 2000, 41, 8451-8455; base-mediated addition of formaldehyde followed by elimination; f) P. Klein, W. L. Nelson, J. Med. Chem. 1991, 34, 2438-2444; g) M. Tada, H. Yamada, A. Kanamori, K. Chiba, J Chem. Soc. Perkin Trans. 1 1993, 239-247; h) M. Schwaebe, R. D. Little, J. Org. Chem. 1996, 61, 3240-3244; i) L. A. Paquette, C. F. Sturino, X. Wang, J. C. Prodoger, D. Koh, J. Am. Chem. Soc. 1996, 118, 5620-5633; other methods; j) E. Krawczyk, A. Skowronska, Heteroat. Chem. 2000, 11, 353-361; reviews; k) P. A. Grieco, Synthesis 1975, 67-82; l) N. Petragnani, H. M. C. Ferraz, G. V. J. Silva, Synthesis 1986, 157-183.
110. Stiles reagent: a) see ref. [9d]; b) J. Martin, P. C. Watts, F. Johnson, J. Org. Chem. 1974, 39, 1676-1681; c) L. A. Paquette, G. D. Annis, H. Schostarez, J. Am. Chem. Soc. 1982, 104, 6646-6653; Eschenmoser salt; d) H. Mattes, K. Hamada, C. Benezra, J. Med. Chem. 1987, 30, 1948-1951; e) I. Marcos, E. Redero, F. Bermejo, Tetrahedron Lett. 2000, 41, 8451-8455; base-mediated addition of formaldehyde followed by elimination; f) P. Klein, W. L. Nelson, J. Med. Chem. 1991, 34, 2438-2444; g) M. Tada, H. Yamada, A. Kanamori, K. Chiba, J Chem. Soc. Perkin Trans. 1 1993, 239-247; h) M. Schwaebe, R. D. Little, J. Org. Chem. 1996, 61, 3240-3244; i) L. A. Paquette, C. F. Sturino, X. Wang, J. C. Prodoger, D. Koh, J. Am. Chem. Soc. 1996, 118, 5620-5633; other methods; j) E. Krawczyk, A. Skowronska, Heteroat. Chem. 2000, 11, 353-361; reviews; k) P. A. Grieco, Synthesis 1975, 67-82; l) N. Petragnani, H. M. C. Ferraz, G. V. J. Silva, Synthesis 1986, 157-183.
111. F. David, J. A. Elix, M. W. Samsudin, Aust. J. Chem. 1990, 43, 1297-1300.