Total Synthesis of ent-Dioxepandehydrothyrsiferol via a Bromonium-Initiated Epoxide-Opening Cascade
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Jamison_Total synthesis.pdf
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Author(s)
Tanuwidjaja, Jessica
Ng, Sze-Sze
Jamison, Timothy F.
Date Issued
August 2009
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Tanuwidjaja, Jessica, Sze-Sze Ng, and Timothy F. Jamison. “Total Synthesis of ent-Dioxepandehydrothyrsiferol via a Bromonium-Initiated Epoxide-Opening Cascade.” Journal of the American Chemical Society 131, no. 34 (September 2, 2009): 12084-12085.
Version
Author's final manuscript
Abstract
In the first total synthesis of ent-dioxepandehydrothyrsiferol, the signature trans-anti-trans 7,7,6-fused tricyclic polyether framework was constructed in a single bromonium-initiated epoxide-opening cascade that incorporates both endo- and exo-selective epoxide openings, each directed by the substitution pattern of the epoxide (methyl groups). This study thus demonstrates the feasibility of a possible biogenesis.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
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DOI of Published Version
https://doi.org/10.1021/ja9052366
