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Oxyanionic sigmatropic rearrangements relevant to cyclooctadienone formation in penostatins I and F.

ABSTRACT: The results of several experiments designed to probe the energetic viability of a reaction path for generation of penostatins I (3) and F (4) via spontaneous [3,3]-sigmatropic rearrangement are reported. In particular, the enolate derived from the 2-vinyl-6-acyldihydropyran 8-cis gave cyclooctadienone 12 via facile anionic oxy-Claisen rearrangement, demonstrating the feasibility of such an event.

SUBMITTER: Jansma MJ

PROVIDER: S-EPMC3501534 | biostudies-literature | 2012 Sep

REPOSITORIES: biostudies-literature

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Oxyanionic sigmatropic rearrangements relevant to cyclooctadienone formation in penostatins I and F.

Jansma Matthew J MJ Hoye Thomas R TR

Organic letters 20120910 18

The results of several experiments designed to probe the energetic viability of a reaction path for generation of penostatins I (3) and F (4) via spontaneous [3,3]-sigmatropic rearrangement are reported. In particular, the enolate derived from the 2-vinyl-6-acyldihydropyran 8-cis gave cyclooctadienone 12 via facile anionic oxy-Claisen rearrangement, demonstrating the feasibility of such an event. ...[more]

PMID: 22963036

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