Issue 20, 2004

Synthesis of anti-tumour phosphatidylinositol analogues from glucose by the use of ring-closing olefin metathesis

Abstract

A divergent strategy is described for synthesis of the novel phosphatidylinositols 13. The synthetic approach commences from benzyl-protected methyl 6-iodo-6-deoxy-α-D-glucopyranoside, which undergoes zinc-mediated reductive fragmentation followed by vinyl Grignard addition and ring-closing metathesis to afford the key conduritol B intermediate 7. This can trifurcate to form three different benzyl-protected myo-inositol headgroups 46, which after phosphorylation and attachment of the glycerolipid part give phosphatidylinositols 13. Preliminary biological testing against human colon adenocarcinoma cells reveals that analogues 13 are significant anti-tumour agents.

Graphical abstract: Synthesis of anti-tumour phosphatidylinositol analogues from glucose by the use of ring-closing olefin metathesis

Article information

Article type
Paper
Submitted
20 Jul 2004
Accepted
10 Aug 2004
First published
16 Sep 2004

Org. Biomol. Chem., 2004,2, 2951-2957

Synthesis of anti-tumour phosphatidylinositol analogues from glucose by the use of ring-closing olefin metathesis

T. L. Andresen, D. M. Skytte and R. Madsen, Org. Biomol. Chem., 2004, 2, 2951 DOI: 10.1039/B411021H

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