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Total Synthesis of (+)-Panacene

Authors :
Caroline L. Nesbitt
Johannes P. Schmidt
Neanne Alnafta
Christopher S. P. McErlean
Source :
Organic letters. 18(24)
Publication Year :
2016

Abstract

The first total synthesis of the naturally occurring enantiomer of the marine bromoallene (+)-panacene is described. Central to this concise enantioselective synthesis was the use of a Noyori transfer hydrogenation for a Dynamic Kinetic Resolution (DKR) that set the desired absolute stereochemistry. A highly stereoselective Julia coupling was then used to install a Z-configured enyne, which enabled the biomimetic construction of the axially chiral bromoallene.

Details

ISSN :
15237052
Volume :
18
Issue :
24
Database :
OpenAIRE
Journal :
Organic letters
Accession number :
edsair.doi.dedup.....ce2e1176fddb64beac5ace43f6f27d7d