1. Total Synthesis of (+)-Panacene
- Author
-
Caroline L. Nesbitt, Johannes P. Schmidt, Neanne Alnafta, and Christopher S. P. McErlean
- Subjects
Enyne ,010405 organic chemistry ,Chemistry ,Stereochemistry ,Organic Chemistry ,Enantioselective synthesis ,Total synthesis ,010402 general chemistry ,Transfer hydrogenation ,01 natural sciences ,Biochemistry ,Combinatorial chemistry ,0104 chemical sciences ,Kinetic resolution ,Stereoselectivity ,Physical and Theoretical Chemistry ,Enantiomer - 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.
- Published
- 2016