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Total synthesis of ent-dioxepandehydrothyrsiferol via a bromonium-initiated epoxide-opening cascade.

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.

SUBMITTER: Tanuwidjaja J

PROVIDER: S-EPMC2760255 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

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Total synthesis of ent-dioxepandehydrothyrsiferol via a bromonium-initiated epoxide-opening cascade.

Tanuwidjaja Jessica J Ng Sze-Sze SS Jamison Timothy F TF

Journal of the American Chemical Society 20090901 34

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. ...[more]

PMID: 19663441

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