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Issue 5, 2010
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Synthesis of phalluside-1 and Sch II using 1,2-metallaterearrangements

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Abstract

(4E,8E,10E)-9-Methyl-4,8,10-sphingatrienine, a core component of marine sphingolipids, was synthesised for the first time using a copper(I)-mediated 1,2-metallate rearrangement of a lithiated glycal as a key step. It was converted to phalluside-1, a cerebroside isolated from the ascidian Phallusia fumigate. By an analogous route, (4E,8E)-9-methyl-4,8-sphingadiene was synthesised and converted to Sch II, a cerebroside that induces fruiting body formation in the basidiomycete Schizophyllum commune.

Graphical abstract: Synthesis of phalluside-1 and Sch II using 1,2-metallate rearrangements

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Article information


Submitted
29 Sep 2009
Accepted
30 Nov 2009
First published
14 Jan 2010

Org. Biomol. Chem., 2010,8, 1188-1193
Article type
Paper

Synthesis of phalluside-1 and Sch II using 1,2-metallate rearrangements

F. J. Black and P. J. Kocienski, Org. Biomol. Chem., 2010, 8, 1188
DOI: 10.1039/B920285D

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