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Stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine [Jaspine B]

Prasad, Pavirayani R and Chandrakumar, Appayee (2007) Stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine [Jaspine B]. In: Journal of Organic Chemistry, 72 (16). pp. 6312-6315.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo0707838


A practical stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) was achieved in 48% overall yield from D-(-)-tartaric acid. Key features of the sequence include the diastereoselective formation of a tetrol with three contiguous chiral centers, which was further elaborated to pachastrissamine. The synthetic route is operationally simple, diastereoselective and is amenable for the synthesis of a number of analogues of pachastrissamine.

Item Type: Journal Article
Publication: Journal of Organic Chemistry
Publisher: American Chemical Society
Additional Information: Copyright of this article belongs to American Chemical Society.
Keywords: asymmetric-synthesis;enantioselective synthesis; enantiospecific synthesis;l-(+)-tartaric acid;marine sponge; phytosphingosine;enantiomers;derivatives;lactones.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 30 Apr 2010 08:57
Last Modified: 19 Sep 2010 06:01
URI: http://eprints.iisc.ac.in/id/eprint/27418

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