Total Synthesis of Tetrahydrolipstatin and Stereoisomers via a Highly Regio- and Diastereoselective Carbonylation of Epoxyhomoallylic Alcohols | Zendy

Michael Mulzer | Zendy; Brandon J. Tiegs | Zendy; Yanping Wang | Zendy; Geoffrey W. Coates | Zendy; George A. O’Doherty | Zendy

Open Access

Total Synthesis of Tetrahydrolipstatin and Stereoisomers via a Highly Regio- and Diastereoselective Carbonylation of Epoxyhomoallylic Alcohols

Author(s) -

Michael Mulzer,

Brandon J. Tiegs,

Yanping Wang,

Geoffrey W. Coates,

George A. O’Doherty

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja505639u

Subject(s) - chemistry , carbonylation , enantioselective synthesis , regioselectivity , epoxide , catalysis , stereochemistry , bimetallic strip , lactone , lewis acids and bases , stereoisomerism , organic chemistry , carbon monoxide

A concise enantioselective synthesis of tetrahydrolipstatin (THL) and seven stereoisomers has been achieved. The synthesis of THL was accomplished in 10 steps and 31% overall yield from an achiral ynone. Key to the success of the approach is the use of a bimetallic [Lewis acid](+)[Co(CO)4](-) catalyst for a late-stage regioselective carbonylation of an enantiomerically pure cis-epoxide to a trans-β-lactone. The success of this route to THL and its stereoisomers also demonstrated the practicality of the carbonylation catalyst for complex molecule synthesis as well as its functional group compatibility.

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