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Org Lett. 2009 Jul 16;11(14):3104-7. doi: 10.1021/ol901213d.

Synthesis of prostaglandin and phytoprostane B1 via regioselective intermolecular Pauson-Khand reactions.

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1
Unitat de Recerca en Síntesi Asimètrica (URSA-PCB), Institute for Research in Biomedicine Universitat de Barcelona, Parc Cientific de Barcelona c/ Baldiri Reixac 10, 08028 Barcelona, Spain.

Abstract

A new approach to the synthesis of prostaglandin and phytoprostanes B(1) is described. The key step is an intermolecular Pauson-Khand reaction between a silyl-protected propargyl acetylene and ethylene. This reaction, promoted by NMO in the presence of 4 A molecular sieves, afforded the 3-tert-butyldimethylsilyloxymethyl-2-substituted-cyclopent-2-en-1-ones (III) in good yield and with complete regioselectivity. Deprotection of the silyl ether, followed by Swern oxidation, gave 3-formyl-2-substituted-cyclopent-2-en-1-ones (II). Julia olefination of the aldehydes II with the suitable chiral sulfone enabled preparation of PPB(1) type I and PGB(1).

PMID:
19545162
DOI:
10.1021/ol901213d
[Indexed for MEDLINE]
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