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Formal total synthesis of (+)-didemniserinolipid B

Prasad, Kavirayani R and Gandi, Vasudeva Rao (2010) Formal total synthesis of (+)-didemniserinolipid B. In: Tetrahedron: Asymmetry, 21 (23). pp. 2848-2852.

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Official URL: http://dx.doi.org/10.1016/j.tetasy.2010.11.006


The formal total synthesis of (+)-didemniserinolipid B, a marine tunicate possessing a 6,8-dioxabicyclo3.2.1]octane framework, was accomplished starting from L-(+)-tartaric acid. The key transformations in the synthesis include the elaboration of a gamma-hydroxy-amide readily obtained by desymmetrization of tartaric acid bis-amide via the controlled addition of a Grignard reagent followed by stereoselective reduction of the resulting ketone. (C) 2010 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Publication: Tetrahedron: Asymmetry
Publisher: Elsevier Science
Additional Information: Copyright of this article belongs to Elsevier Science.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 12 Apr 2011 09:11
Last Modified: 12 Apr 2011 09:11
URI: http://eprints.iisc.ac.in/id/eprint/35965

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