Synlett 2012; 23(11): 1625-1628
DOI: 10.1055/s-0031-1290379
letter
© Georg Thieme Verlag Stuttgart · New York

An Enantioselective Mukaiyama Aldol Reaction as the Key Step towards the Tetrahydropyran Core of Psymberin via a γ-Butyrolactone Intermediate

Max Bielitza
Institut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Stetternicher Forst, Geb. 15.8, 52426 Jülich, Germany, Fax: +49(2461)616196   Email: j.pietruszka@fz-juelich.de
,
Jörg Pietruszka*
Institut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Stetternicher Forst, Geb. 15.8, 52426 Jülich, Germany, Fax: +49(2461)616196   Email: j.pietruszka@fz-juelich.de
› Author Affiliations
Further Information

Publication History

Received: 30 March 2012

Accepted after revision: 23 April 2012

Publication Date:
14 June 2012 (online)


Abstract

We report an alternative synthetic route towards the tetrahydropyran core of psymberin. The key steps are a catalytic enantioselective Mukaiyama aldol reaction and a syn reduction, which allowed for the rapid assembly of a γ-lactone as a precursor for the central fragment of the natural product.