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

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• 作者：Michael Mulzer ; Brandon J. Tiegs ; Yanping Wang ; Geoffrey W. Coates ; George A. O鈥橠oherty
• 刊名：Journal of the American Chemical Society
• 出版年：2014
• 出版时间：July 30, 2014
• 年：2014
• 卷：136
• 期：30
• 页码：10814-10820
• 全文大小：603K
• ISSN：1520-5126

文摘

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]^{鈭?/sup> catalyst for a late-stage regioselective carbonylation of an enantiomerically pure cis-epoxide to a trans-尾-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.}