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A formal synthesis of (-)-englerin A by relay ring closing metathesis and transannular etherification.

ABSTRACT: A bicyclization approach to englerin A has culminated in a formal asymmetric total synthesis. Key transformations in the 10-step sequence are a regiospecific epoxide opening and a relay ene-yne-ene metathesis that converts linear substrates specifically to ?(4,6)-guaiadiene-9,10 diol derivatives. Regiospecific functionalization of the diene moiety installs the oxygen bridge required for the englerin tricyclic core.

SUBMITTER: Lee J 

PROVIDER: S-EPMC3390928 | biostudies-literature | 2012 Jun

REPOSITORIES: biostudies-literature

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A formal synthesis of (-)-englerin A by relay ring closing metathesis and transannular etherification.

Lee Jungyong J   Parker Kathlyn A KA  

Organic letters 20120507 11

A bicyclization approach to englerin A has culminated in a formal asymmetric total synthesis. Key transformations in the 10-step sequence are a regiospecific epoxide opening and a relay ene-yne-ene metathesis that converts linear substrates specifically to Δ(4,6)-guaiadiene-9,10 diol derivatives. Regiospecific functionalization of the diene moiety installs the oxygen bridge required for the englerin tricyclic core. ...[more]

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