Enantioselective synthesis of ent-stellettamide A via a novel dipolar cycloaddition reaction of (trimethylsilyl)diazomethane

Journal of Organic Chemistry

Volumn 62, Issue 23, 1997, Pages 7916-7917

  Whitlock, Gavin A ^a   Carreira, Erick M ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIAZOMETHANE; STELLETTAMIDE A; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; AROMATIZATION; ARTICLE; CYTOTOXICITY; DRUG ISOLATION; DRUG SYNTHESIS; ENANTIOMER; EPITHELIUM CELL; NONHUMAN;

EID: 0030724652     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971571l     Document Type: Article

References (20)

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5. For recent advances in methodology aimed at the preparation of indohzidines, see: (a) Li, Y. W.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707. (b) Ciufolini, M. A.; Roschangar, F. J. Am. Chem. Soc. 1996, 118, 12082. Comins, D. L.; Zhang, Y. J. Am. Chem. Soc. 1996, 118, 12248.
6. For recent advances in methodology aimed at the preparation of indohzidines, see: (a) Li, Y. W.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707. (b) Ciufolini, M. A.; Roschangar, F. J. Am. Chem. Soc. 1996, 118, 12082. Comins, D. L.; Zhang, Y. J. Am. Chem. Soc. 1996, 118, 12248.
7. For general references, see: (a) Carruthers, W. Cycloaddition Reactions in Organic Sythesis; Pergammon: Oxford, 1990; p 269. (b) Padwa, A. In Comprehensive Organic Synthesis; Trost, B., Ed.; Wiley: New York, 1991; Vol. 4, p 1069. Wade, P. A. In Comprehensive Organic Synthesis; Trost, B., Ed.; Wiley: New York, 1991; Vol. 4, p 1111. Little, R. D. In Comprehensive Organic Synthesis; Trost, B., Ed.; Wiley: New York, 1991; Vol. 5, p 239.
8. For general references, see: (a) Carruthers, W. Cycloaddition Reactions in Organic Sythesis; Pergammon: Oxford, 1990; p 269. (b) Padwa, A. In Comprehensive Organic Synthesis; Trost, B., Ed.; Wiley: New York, 1991; Vol. 4, p 1069. Wade, P. A. In Comprehensive Organic Synthesis; Trost, B., Ed.; Wiley: New York, 1991; Vol. 4, p 1111. Little, R. D. In Comprehensive Organic Synthesis; Trost, B., Ed.; Wiley: New York, 1991; Vol. 5, p 239.
9. For general references, see: (a) Carruthers, W. Cycloaddition Reactions in Organic Sythesis; Pergammon: Oxford, 1990; p 269. (b) Padwa, A. In Comprehensive Organic Synthesis; Trost, B., Ed.; Wiley: New York, 1991; Vol. 4, p 1069. Wade, P. A. In Comprehensive Organic Synthesis; Trost, B., Ed.; Wiley: New York, 1991; Vol. 4, p 1111. Little, R. D. In Comprehensive Organic Synthesis; Trost, B., Ed.; Wiley: New York, 1991; Vol. 5, p 239.
10. For general references, see: (a) Carruthers, W. Cycloaddition Reactions in Organic Sythesis; Pergammon: Oxford, 1990; p 269. (b) Padwa, A. In Comprehensive Organic Synthesis; Trost, B., Ed.; Wiley: New York, 1991; Vol. 4, p 1069. Wade, P. A. In Comprehensive Organic Synthesis; Trost, B., Ed.; Wiley: New York, 1991; Vol. 4, p 1111. Little, R. D. In Comprehensive Organic Synthesis; Trost, B., Ed.; Wiley: New York, 1991; Vol. 5, p 239.
11. For a comprehensive review of asymmetric dipolar cycloadditions, see: Cinquini, M., Cozzi, F. Formation of C-C Bonds by [3+2] Cycloadditions. In Stereoselective Synthesis; Helmchen, G., Hoffman, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 5, p 2953.
12. Mish, M. R.; Guerra, F. M.; Carreira, E. M. J. Am. Chem. Soc. 1997, 119, 8379.
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14. (b) Seyferth, D.; Menzel, H.; Dow, A. W.; Flood, T. C. J. Organomet. Chem. 1972, 44, 279.
15. 2. The stereochemistry of the adducts is consistent with the models that have been previously proposed; see: Kim, B. H.; Curran, D. P. Tetrahedron 1993, 49, 293.
16. Mandai, T.; Matsumoto, T.; Tsujiguchi, Y.; Matsuoka, S.; Tsuji, J. J. Organomet. Chem. 1994, 473, 343.
17. Stoilova, V.; Trifonov, L. S.; Orahovats, A. S. Synthesis 1979, 105.
18. 1H NMR spectroscopy (Myers, A. G.; Yang, B. H.; Chen, H.; Gleason, J. L. J. Am. Chem. Soc. 1994, 116, 9361). Reduction of the alkylation product to the corresponding aldehyde followed by condensation with (carbethoxy-methylene)triphenylphosphorane gave the ethyl esters of 19 and ent-19, which were subsequently saponified (LiOH, THF) to furnish 19 and ent-19.
19. We are grateful to Prof. Fusetani for generously furnishing us with authentic natural stellettamide A.
20. 2 to give the monobasic phosphate salt, which was shown to be identical with stellettamide A by spectroscopic methods.