A short and efficient synthesis of 1-deoxy-castanospermine and 1-deoxy-8a-epi-castanospermine

Patil, Nitin T. ; Tilekar, Jayant N. ; Dhavale, Dilip D. (2001) A short and efficient synthesis of 1-deoxy-castanospermine and 1-deoxy-8a-epi-castanospermine Tetrahedron Letters, 42 (4). pp. 747-749. ISSN 0040-4039

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

Related URL: http://dx.doi.org/10.1016/S0040-4039(00)02103-1

Abstract

A new route for the synthesis of 1-deoxy-castanospermine 2 and 1-deoxy-8a-epi-castanospermine 3 has been developed via a sequential triple reductive amination process of a suitably protected D-gluco-oct-5-ulo-1,8-dialdose, which was easily prepared by three carbon homologation of readily available α-D-xylo-pentodialdose using an appropriate Grignard reagent followed by oxidation.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Alkaloids; Indolizidine; Enzyme Inhibitors; Grignard Reaction
ID Code:9623
Deposited On:02 Nov 2010 11:17
Last Modified:01 Jun 2011 10:31

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