Towards a total synthesis of guanacastepene A: Construction of fully functionalized AB and BC ring segments

Tetrahedron Letters

Volumn 43, Issue 39, 2002, Pages 6975-6978

  Mehta, Goverdhan ^a   Umarye, Jayant D ^a   Gagliardini, Vanessa ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; GUANACASTEPENE A; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; DRUG SYNTHESIS; EPOXIDATION; OXIDATION; STEREOCHEMISTRY;

EID: 0037163284     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01597-6     Document Type: Article

References (24)

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10. Since the preparation of this manuscript, the following additional studies directed towards the synthesis of guanacastepene A have come to our attention. See: (a) Shipe, W. D.; Sorensen, E. J. Org. Lett. 2002, 4, 2063; (b) Nguyen, T. M.; Lee, D. Tetrahedron Lett. 2002, 43, 4033.
11. Since the preparation of this manuscript, the following additional studies directed towards the synthesis of guanacastepene A have come to our attention. See: (a) Shipe, W. D.; Sorensen, E. J. Org. Lett. 2002, 4, 2063; (b) Nguyen, T. M.; Lee, D. Tetrahedron Lett. 2002, 43, 4033.
12. During the review process of this paper, a total synthesis of guanacastepene A by Danishefsky and co-workers has appeared. See: (a) Tan, D. S.; Dudley, G. B.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 2185; (b) Lin, S.; Dudley, G. B.; Tan, D. S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 2188.
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14. +-H-OAc, 190).
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19. 13 formulated earlier as having the all cis arrangement of the two hydroxyl groups as well as the angular methyl group. As it turns out now the secondary hydroxyl group and the angular methyl group have the requisite trans relationship present in the natural product.
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24. o) and 0.0718 for all 2335 data. Crystallographic data has been deposited in the Cambridge Crystallographic Data Center, CCDC 183724.