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A Short Diastereoselective Total Synthesis of (±)-Vibralactone.

Authors :
Leeder AJ
Heap RJ
Brown LJ
Franck X
Brown RC
Source :
Organic letters [Org Lett] 2016 Dec 02; Vol. 18 (23), pp. 5971-5973. Date of Electronic Publication: 2016 Oct 31.
Publication Year :
2016

Abstract

A total synthesis of the (±)-vibralactone has been achieved in 11 steps and 16% overall yield from malonic acid. Key steps include a highly diastereoselective allylation of an α-formyl ester containing an all carbon α-quaternary center, a Pd-catalyzed deallylative β-lactonization, and an aldehyde-selective Wacker oxidation of a terminal alkene.

Details

Language :
English
ISSN :
1523-7052
Volume :
18
Issue :
23
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
27797210
Full Text :
https://doi.org/10.1021/acs.orglett.6b03007