Pharmacophore Mapping in the Laulimalide Series: Total Synthesis of a Vinylogue for a Late-Stage Metathesis Diversification Strategy
Organic Letters2006Vol. 8(18), pp. 4105–4108
Citations Over TimeTop 14% of 2006 papers
Abstract
An efficient synthesis of the macrocyclic core of laulimalide with a pendant vinyl group at C20 is described, allowing for late-stage introduction of various side chains through a selective and efficient cross metathesis diversification step. Representative analogues reported herein are the first to contain modifications to only the side chain dihydropyran of laulimalide and des-epoxy laulimalide. This step-economical strategy enables the rapid synthesis of new analogues using alkenes as an inexpensive, abundantly available diversification feedstock.
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