PubAg

Main content area

A Formal Synthesis of (−)-Englerin A by Relay Ring Closing Metathesis and Transannular Etherification

Author:
Lee, Jungyong, Parker, Kathlyn A.
Source:
Organic letters 2012 v.14 no.11 pp. 2682-2685
ISSN:
1523-7052
Subject:
chemical reactions, moieties, organic compounds, oxygen, regioselectivity
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 Δ⁴,⁶-guaiadiene-9,10 diol derivatives. Regiospecific functionalization of the diene moiety installs the oxygen bridge required for the englerin tricyclic core.
Agid:
5783834