Synthesis of chiral 4-hydroxy-2,3-unsaturated carbonyl compounds from 3,4-epoxy alcohols by oxidation: application in the formal synthesis of macrosphelide A

Chakraborty, Tushar K. ; Purkait, Subhas ; Das, Sanjib (2003) Synthesis of chiral 4-hydroxy-2,3-unsaturated carbonyl compounds from 3,4-epoxy alcohols by oxidation: application in the formal synthesis of macrosphelide A Tetrahedron, 59 (46). pp. 9127-9135. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/j.tet.2003.09.070

Abstract

An interesting transformation during the oxidation of 3,4-epoxy alcohols 1a-d, derived from the corresponding homoallylic alcohols, led to the formation of 4-hydroxy-2,3-unsaturated carbonyls 2a-d in very good yields. One of these products 2c was transformed into the functionalised carboxylic acid 5, an advanced stage intermediate from which the total synthesis of macrosphelide A has been reported.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Epoxy Alcohols; Sharpless Epoxidation; Epoxide Opening; Macrosphelides
ID Code:20573
Deposited On:20 Nov 2010 14:17
Last Modified:22 May 2011 15:08

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