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  • Title: Pharmacophore mapping in the laulimalide series: total synthesis of a vinylogue for a late-stage metathesis diversification strategy.
    Author: Wender PA, Hilinski MK, Skaanderup PR, Soldermann NG, Mooberry SL.
    Journal: Org Lett; 2006 Aug 31; 8(18):4105-8. PubMed ID: 16928085.
    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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