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Synthesis of 9-oxa-noradamantane derivative, an aesthetically pleasing 'oxa-basket'
, Ch.N. Rao
Published in
2009
Volume: 50
   
Issue: 41
Pages: 5751 - 5753
Abstract
A simple protocol for the synthesis of an aesthetically pleasing 'oxa-basket' (5-methoxy-2,8,13-trioxapentacyclo[7.2.1.1.5,120.4,1106,10]tridecane-3,7-dione), possessing 9-oxa-noradamantane core, is described. The readily available diquinane based dichloro bis-γ-lactone precursor upon treatment with MeSO3H furnished dichloro 'oxa-basket' which was dechlorinated using TBTH/AIBN to obtain the title compound. The key role of the chlorines was demonstrated by replacement with hydrogen or allyl substituents which redirects the cascade to simple hydrolysis products. © 2009 Elsevier Ltd. All rights reserved.
About the journal
JournalTetrahedron Letters
ISSN00404039