Pharmacophore mapping in the laulimalide series: Total synthesis of a vinylogue for a late-stage metathesis diversification strategy

Paul A. Wender, Michael K. Hilinski, Philip R. Skaanderup, Nicolas G. Soldermann, Susan L. Mooberry

Research output: Contribution to journalArticle

25 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)4105-4108
Number of pages4
JournalOrganic Letters
Volume8
Issue number18
DOIs
StatePublished - Aug 31 2006
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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