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 |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 80329 |
| Deposited On: | 31 Jan 2012 14:29 |
| Last Modified: | 31 Jan 2012 14:29 |
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