Synthesis of 9-oxa-noradamantane derivative, an aesthetically pleasing 'oxa-basket'

Khan, Faiz Ahmed ; Nageswara Rao, Ch. (2009) Synthesis of 9-oxa-noradamantane derivative, an aesthetically pleasing 'oxa-basket' Tetrahedron Letters, 50 (41). pp. 5751-5753. ISSN 0040-4039

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.tetlet.2009.07.143

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.

Item Type:Article
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ID Code:80329
Deposited On:31 Jan 2012 14:29
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