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. 2010 Sep 3;12(17):3890-3.
doi: 10.1021/ol1015898.

Synthesis of the bis-tetrahydropyran core of amphidinol 3

Michael T Crimmins  1 , Timothy J Martin, Theodore A Martinot
Affiliations

Synthesis of the bis-tetrahydropyran core of amphidinol 3

Michael T Crimmins et al. Org Lett. .

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.

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Figures

Scheme 1
Scheme 1
Retrosynthetic Analysis
Scheme 2
Scheme 2
Synthesis of Tetrahydropyran 5 and Elaboration to β-ketophosphonate 3
Scheme 3
Scheme 3
Synthesis of Aldehyde 4 and Fragment Coupling
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