A ring-closing metathesis approach to the bicyclo[4.3.1]decane core of caryolanes

William Goldring, Warren Paden

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

A synthesis of highly substituted and sterically congested bicyclo[4.3.1]decenes, a structure embedded in the core 4,7,6-tricyclic system of natural caryolanes, was successfully achieved via a ring-closing metathesis (RCM) reaction of syn-1,3-diene substituted cyclohexanols. The construction of the diene substrates, starting from 4-acetoxy-3-methyl-2-cyclohexen-1-one, employed diastereoselective copper-mediated conjugate addition and Grignard reactions. An X-ray crystal structure determination of a key synthetic intermediate confirmed the relative stereochemistry of the RCM bicyclic product.
Original languageEnglish
Pages (from-to)859-862
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number8
DOIs
Publication statusPublished - 23 Feb 2011

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