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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