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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-other | 2010 Sep

REPOSITORIES: biostudies-other

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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]

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