Khan, Faiz Ahmed ; Dash, Jyotirmayee ; Sahu, Nilam ; Sudheer, Ch. (2002) An easy access to γ-lactone-fused cyclopentanoids Journal of Organic Chemistry, 67 (11). pp. 3783-3787. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo025521e
Related URL: http://dx.doi.org/10.1021/jo025521e
Abstract
The tricyclic α-keto hemiacetals 3a,b and 8a-d obtained from ruthenium-catalyzed oxidation of tetrahalonorbornyl derivatives possessing a pendant hydroxymethyl group were cleaved using Pb(OAc)4 or alkaline H2O2 to give γ-lactone-fused cyclopentane derivatives 5a,b and 9a-d. The α-keto hemiacetal 3b has also been elaborated to spiroepoxide derivative 25. The stable hydrate 4 formed from ruthenium-catalyzed oxidation of acrolein adduct 10 furnished an intramolecular hemiacetal 11 upon cleavage with Pb(OAc)4. The α-halo ester moiety in 5a was transformed smoothly in a highly regio- and stereoselective manner to α-hydroxy esters through a lactone-assisted intermediate to furnish 18.
Item Type: | Article |
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Source: | Copyright of this article belongs to American Chemical Society. |
ID Code: | 79665 |
Deposited On: | 27 Jan 2012 14:50 |
Last Modified: | 27 Jan 2012 14:50 |
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