Synthesis 2013; 45(13): 1863-1869
DOI: 10.1055/s-0033-1338706
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Febrifugine and a Formal Synthesis of (+)-Halofuginone Employing an Organocatalytic Direct Vinylogous Aldol Reaction

Sunil V. Pansare*
Department of Chemistry, Memorial University, St. John’s, NL, A1B 3X7, Canada   Fax: +91(709)8643702   Email: spansare@mun.ca
,
Eldho K. Paul
Department of Chemistry, Memorial University, St. John’s, NL, A1B 3X7, Canada   Fax: +91(709)8643702   Email: spansare@mun.ca
› Author Affiliations
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Publication History

Received: 19 February 2013

Accepted after revision: 14 April 2013

Publication Date:
08 May 2013 (online)


Dedicated to Professor Scott E. Denmark on the occasion of his 60th birthday

Abstract

The enantioselective organocatalytic direct vinylogous aldol reaction of γ-crotonolactone and a suitable aldehyde was utilized in the synthesis of a functionalized γ-butenolide. The γ-butenolide (aldol product) was stereoselectively converted into a 5-aminoalkyl butyrolactone, which isomerized to the key 2,3-disubstituted piperidinone, a common intermediate to (+)-febrifugine and (+)-halofuginone.

Supporting Information