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An Unusual Ring‐Contraction/Rearrangement Sequence for Making Functionalized Di‐ and Triquinanes
Author(s) -
Nagaraju Chinta,
Prasad Kavirayani R.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201407680
Subject(s) - chemistry , contraction (grammar) , sequence (biology) , stereochemistry , cope rearrangement , lewis acids and bases , ring (chemistry) , rearrangement reaction , organic chemistry , biology , catalysis , biochemistry , endocrinology
A novel ring contraction/rearrangement sequence leading to functionalized 2,8‐oxymethano‐bridged di‐ and triquinane compounds is observed in the reaction of various substituted 1‐methyl‐4‐isopropenyl‐6‐oxabicylo[3.2.1]octan‐8‐ones with Lewis acids. The reaction is novel and is unprecedented for the synthesis of di‐ and triquinane frameworks.