1. Asymmetric Catalysis Route to anti,anti Stereotriads, Illustrated by Applications
- Author
-
Qiuzhe Xie and Kathlyn A. Parker
- Subjects
Ephedrine ,Biological Products ,Molecular Structure ,Chemistry ,Stereochemistry ,Organic Chemistry ,Scytophycin C ,Enantioselective synthesis ,Stereoisomerism ,Sequence (biology) ,Bridged Bicyclo Compounds, Heterocyclic ,Biochemistry ,Catalysis ,Lactones ,Polyketide ,Aplyronine A ,Depsipeptides ,Serine ,Macrolides ,Physical and Theoretical Chemistry ,Enantiomer ,Chirality (chemistry) - Abstract
A short sequence based on asymmetric catalysis, chirality transfer, and an optimized carbometallation protocol gave an anti,anti stereotriad building block in six steps. Both enantiomers of the chirality source, N-methyl ephedrine, are inexpensive, and the auxiliary is recoverable. In one chiral series, the building block was converted to the "B-2" intermediate in Miyashita's synthesis of scytophycin C; in the enantiomeric series, it was converted to a key intermediate for aplyronine A and to the polyketide "cap" for the callipeltins.
- Published
- 2008