Elucidation of the Sharpless epoxidation of zerumbol

The Sharpless asymmetric epoxidation of (+)-zerumbol, itself obtained by the reduction of zerumbone 1 gave only all- erythro bisepoxide 3 which has five stereogenic centers. Chiral monoepoxide 4, which decomposed easily under acidic or high-temperature conditions, could also be obtained. The reactio...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2006-09, Vol.17 (16), p.2311-2316
Main Authors: Kitayama, Takashi, Furuya, Atsushi, Moriyama, Chiyuki, Masuda, Tomomi, Fushimi, Sachiko, Yonekura, Yuji, Kubo, Haruko, Kawai, Yasushi, Sawada, Seiji
Format: Article
Language:English
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Summary:The Sharpless asymmetric epoxidation of (+)-zerumbol, itself obtained by the reduction of zerumbone 1 gave only all- erythro bisepoxide 3 which has five stereogenic centers. Chiral monoepoxide 4, which decomposed easily under acidic or high-temperature conditions, could also be obtained. The reaction mechanism was revealed to be diastereoselective but non-enantioselective monoepoxidation at the 2,3-position, which proceeded quantitatively followed by a second epoxidation at the 10,11-position, and also proceeded extremely enantioselectively giving an efficient kinetic resolution. Novel asymmetric diepoxydihydroxyzerumbol 6 and triepoxyzerumbol 7 each with seven stereogenic centers were formed with complete diastereoselectivity by dihydroxylation and epoxidation of bisepoxyzerumbol, respectively.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2006.06.049