4b-Aryltetrahydroindeno[1,2-a]indenes by Acid-Catalyzed Transannular Cyclization of Benzannulated Cyclooctene Alcohols
作者:Poonsakdi Ploypradith、Poramate Songthammawat、Tanawat Phumjan、Somsak Ruchirawat
DOI:10.1055/a-1778-8143
日期:2022.9
By starting from two simple building blocks, benzannulated cyclooctenones were obtained in three steps. Subsequent Grignard/aryl lithium addition to the ketone yielded the corresponding tertiary alcohols that underwent stereoselective acid-catalyzed transannular cyclization to provide a cis-fused 5/5 bicyclic indanylindane framework exclusively. Subsequent stereoselective nucleophilic addition to the
通过从两个简单的结构单元开始,分三步获得苯环化环辛酮。随后将格氏/芳基锂添加到酮中产生相应的叔醇,该叔醇经历了立体选择性酸催化的环环环化,仅提供顺式稠合的5/5 双环茚满烷基骨架。随后通过氢化物、水或富电子芳烃对茚满基阳离子进行立体选择性亲核加成,以反式-C9-C9a 形式以良好至优异的产率(高达 92%)提供 4b-芳基四氢茚并[1,2- a ]茚高达 >99:1 的非对映体比例。