Pharmacophore mapping in the laulimalide series: total synthesis of a vinylogue for a late-stage metathesis diversification strategy |
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| Authors: | Wender Paul A Hilinski Michael K Skaanderup Philip R Soldermann Nicolas G Mooberry Susan L |
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| Institution: | Departments of Chemistry and Molecular Pharmacology, Stanford University, Stanford, CA 94305-5080, USA. wenderp@stanford.edu |
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| 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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