The total synthesis and structural revision of stagonolide D

Vadhadiya, Paresh M. ; Puranik, Vedavati G. ; Ramana, C. V. (2012) The total synthesis and structural revision of stagonolide D The Journal of Organic Chemistry, 77 (5). pp. 2169-2175. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo202138g

Related URL: http://dx.doi.org/10.1021/jo202138g

Abstract

The total synthesis of the putative structure of stagonolide D has been completed. The relative and absolute configuration of stagonolide D was established by synthesizing its optical antipode. The adopted strategy involves the construction of the central macrolide employing ring-closing metathesis (RCM), followed by selective protecting group manipulations and a final concomitant −OTBS deprotection and displacement of an −OMs placed next to it, resulting in the formation of the epoxide ring.

Item Type:Article
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ID Code:106008
Deposited On:01 Feb 2018 16:53
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