The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the southern hemisphere EF segment??

Organic & Biomolecular Chemistry Pub Date: 2005-05-24 DOI: 10.1039/B504149J

Abstract

The fully functionalised C29–C51 southern hemisphere of altohyrtin A/spongistatin 1 (1), incorporating the E- and F-ring tetrahydropyran rings and the unsaturated side chain, has been synthesised in a highly convergent and stereocontrolled manner. Key steps in the synthesis of this phosphonium salt include four highly diastereoselective, substrate-controlled, boron aldol reactions to establish key C–C bonds and accompanying stereocentres, where the introduction of the chlorodiene side chain and the C47 hydroxyl-bearing centre were realised by exploiting remote stereoinduction from the F-ring tetrahydropyran.

Graphical abstract: The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the southern hemisphere EF segment
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