Synthesis 2013; 45(8): 1106-1114
DOI: 10.1055/s-0032-1318440
paper
© Georg Thieme Verlag Stuttgart · New York

Enantiomerically Pure Allylboronic Esters as Versatile Reagents in the Enantioselective Synthesis of Dihydro-α-pyrone-Containing Natural Products

Sean Bartlett
a   School of Chemistry, University of Bristol, Cantock’s Close, Bristol BS8 1TS, UK
,
Dietrich Böse
b   Institut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Stetternicher Forst, Geb. 15.8, 52426 Jülich, Germany   Fax: +49(2461)611669   Email: j.pietruszka@fz-juelich.de
,
Daniel Ghori
b   Institut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Stetternicher Forst, Geb. 15.8, 52426 Jülich, Germany   Fax: +49(2461)611669   Email: j.pietruszka@fz-juelich.de
,
Bastian Mechsner
b   Institut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Stetternicher Forst, Geb. 15.8, 52426 Jülich, Germany   Fax: +49(2461)611669   Email: j.pietruszka@fz-juelich.de
,
Jörg Pietruszka*
b   Institut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Stetternicher Forst, Geb. 15.8, 52426 Jülich, Germany   Fax: +49(2461)611669   Email: j.pietruszka@fz-juelich.de
› Author Affiliations
Further Information

Publication History

Received: 29 January 2013

Accepted after revision: 19 February 2013

Publication Date:
07 March 2013 (online)


Abstract

A short and efficient enantio- and diastereoselective synthesis­ of different representatives from the class of dihydro-α-pyrone natural products, including both enantiomers of goniothalamin, massoia lactone, parasorbic acid, and some derivatives is presented. It is based on the application of enantiopure α-chiral allylboronic esters in allyl additions.

Supporting Information

 
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