Efficient stereoselective synthesis of the enantiomers of highly substituted paraconic acids

Journal of Organic Chemistry

Volumn 61, Issue 18, 1996, Pages 6450-6453

  Martín, Tomás ^a   Rodríguez, Carmen M ^a   Martín, Victor S ^a  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; DIHYDROPROTOLICHESTERINIC ACID; GAMMA BUTYROLACTONE DERIVATIVE; METHYLENOLACTOCIN; PROTOLICHESTERINIC ACID; ROCELLARIC ACID; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; TECHNIQUE;

EID: 0029789618     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9606970     Document Type: Article

References (26)

1. For reviews concerning the synthesis of butenolides and saturated γ-lactones see: (a) Nagao, Y.; Dai, W.; Ochiai, M.; Shiro, M. J. Org. Chem. 1989, 54, 5211 and references cited therein. (b) Corey, E. J.; Cheng, X. M. In The Logic of Chemical Synthesis; John Wiley & Sons, Inc.: New York, 1989.
2. For reviews concerning the synthesis of butenolides and saturated γ-lactones see: (a) Nagao, Y.; Dai, W.; Ochiai, M.; Shiro, M. J. Org. Chem. 1989, 54, 5211 and references cited therein. (b) Corey, E. J.; Cheng, X. M. In The Logic of Chemical Synthesis; John Wiley & Sons, Inc.: New York, 1989.
3. (a) Rodríguez, C. M.; Martín, V. S. Tetrahedron Lett. 1991, 32, 2165.
4. (b) Rodríguez, C. M.; Martín, T.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 1994, 59, 4461 and references cited therein.
5. Dictionary of Organic Compounds; Chapman and Hall: New York, 1982. Comprehensive Medicinal Chemistry; Hansch, C., Ed.; Pergamon Press: Oxford, U.K., 1990.
6. Dictionary of Organic Compounds; Chapman and Hall: New York, 1982. Comprehensive Medicinal Chemistry; Hansch, C., Ed.; Pergamon Press: Oxford, U.K., 1990.
7. Mori, K.; Yamane, K. Tetrahedron 1982, 38, 2919.
8. Park, B. K.; Nakagawa, M.; Hirota, A.; Nakayama, M. J. Antibiot. 1988, 47, 751.
9. Murta, M. M.; Azevedö, M. B. M.; Greene, A. E. J. Org. Chem. 1993, 58, 7537.
10. Mulzer, J.; Salimi, N.; Hartl, H. Tetrahedron: Asymmetry 1993, 4, 457.
11. (a) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087.
12. (b) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628.
13. (c) Which this paper was under review a new synthesis of paraconic acids was reported: Sibi, M. P.; Deshpande, P. K.; La Loggia, A. J. Synlett 1996, 343
14. Katsuki, T.; Martín, V. S. Org. React. 1996, 48, 1.
15. Vedejs, E.; Larsen, S. Org. Synth. 1986, 64, 127.
16. Although the observed stereoselectivity is irrelevant for the present work we have full evidence of the stereochemistry of the created stereocenter by conversion into 7 in which the relative stereochemistry is well determined by NOE studies. For a similar rearrangement, see: (a) Burke, S. D.; Pacofsky, G. J.; Piscopio, A. D. Tetrahedron Lett. 1986, 27, 3345. (b) Burke, S. D.; Pacofsky, G. J.; Piscopio, A. D. J. Org. Chem. 1992, 57, 2228. (Matrix Presented)
17. Although the observed stereoselectivity is irrelevant for the present work we have full evidence of the stereochemistry of the created stereocenter by conversion into 7 in which the relative stereochemistry is well determined by NOE studies. For a similar rearrangement, see: (a) Burke, S. D.; Pacofsky, G. J.; Piscopio, A. D. Tetrahedron Lett. 1986, 27, 3345. (b) Burke, S. D.; Pacofsky, G. J.; Piscopio, A. D. J. Org. Chem. 1992, 57, 2228. (Matrix Presented)
18. (a) Saito, S.; Hasegana, T.; Inada, M.; Nishida, R.; Fujii, T.; Nomizu, S.; Moriwake, T. Chem. Lett. 1984, 1384.
19. Lemieux, R. U.; von Rudloff, E. Can. J. Chem. 1955, 33, 1701.
20. Uemura, S. In Comprehensive Organic Synthesis; Trost, B. M., et al., Eds.; Pergamon Press: New York, 1991; Vol. 7, pp 757-787.
21. Flippin, L. A.; Dombroski, M. A. Tetrahedron Lett. 1985, 26, 2977.
22. (a) Núñez, M. T.; Martín, V. S. J. Org. Chem. 1990, 55, 1928.
23. (b) Carlsen, P. H.; Katsuki, T.; Martín, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
24. (a) Huneck, S.; Follmann, G. Z. Naturforsch. B 1967, 57, 666.
25. (b) Asano, M.; Azumi, T. Ber. Dtsch. Chem. Ges. 1935, 68, 995.
26. (c) Asahina, Y.; Yanagita, M. Ibid. 1936, 69, 120.