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Synthesis of the bis-tetrahydropyran core of amphidinol 3.

ABSTRACT: A convergent synthesis of the C31-C52 bis-tetrahydropyran core of the natural product amphidinol 3 is reported. A common intermediate was synthesized from d-tartaric acid utilizing an asymmetric glycolate alkylation/ring-closing metathesis sequence to construct the THP rings. Differential elaboration of the common intermediate allowed the synthesis of two distinct coupling partners which were joined through a modified Horner-Wadsworth-Emmons olefination to provide the bis-tetrahydropyran core.

SUBMITTER: Crimmins MT

PROVIDER: S-EPMC2929927 | biostudies-literature | 2010 Sep

REPOSITORIES: biostudies-literature

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Synthesis of the bis-tetrahydropyran core of amphidinol 3.

Crimmins Michael T MT Martin Timothy J TJ Martinot Theodore A TA

Organic letters 20100901 17

A convergent synthesis of the C31-C52 bis-tetrahydropyran core of the natural product amphidinol 3 is reported. A common intermediate was synthesized from d-tartaric acid utilizing an asymmetric glycolate alkylation/ring-closing metathesis sequence to construct the THP rings. Differential elaboration of the common intermediate allowed the synthesis of two distinct coupling partners which were joined through a modified Horner-Wadsworth-Emmons olefination to provide the bis-tetrahydropyran core. ...[more]

PMID: 20795745

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