Approach to Merosesquiterpenes via Lewis Acid Catalyzed Nazarov-Type Cyclization: Total Synthesis of Akaol A

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• 作者：Badrinath N. Kakde ; Nivesh Kumar ; Pradip Kumar Mondal ; Alakesh Bisai
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：April 15, 2016
• 年：2016
• 卷：18
• 期：8
• 页码：1752-1755
• 全文大小：427K
• 年卷期：0
• ISSN：1523-7052

文摘

A Lewis acid catalyzed Nazarov-type cyclization of arylvinylcarbinol has been developed for the asymmetric synthesis of carbotetracyclic core of merosesquiterpenes. The reaction works only in the presence of 2 mol % of Sn(OTf)₂ and Bi(OTf)₃ in dichloroethane under elevated temperature. The methodology offers the synthesis of a variety of enantioenriched arylvinylcarbinols from commercially available (3aR)-sclareolide 9 in six steps with an eventual concise total synthesis of marine sesquiterpene quinol, akaol A (1a).