Synthesis of phalluside-1 and Sch II using 1,2-metallate rearrangements.
Fiona J Black, Philip J Kocienski
Index: Org. Biomol. Chem. 8(5) , 1188-93, (2010)
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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.
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