Total synthesis of nominal (11S)- and (11R)-cyclocinamide A.

ABSTRACT: The cyclocinamides possess a unique β(2)αβ(2)α 14-membered tetrapeptide core. The initially reported biological data and intriguing structure, which was without full stereochemical identification, necessitated synthesis of both nominal (all-S) cyclocinamide A and the 11R isomer. The completed synthesis is highlighted by the use of a (cyclo)asparagine-containing dipeptide as a turn inducing fragment. Due to inconsistencies in analytical data between natural and synthetic samples, a re-evaluation of the natural product stereochemistry appears necessary.

SUBMITTER: Garcia JM 

PROVIDER: S-EPMC3347969 | biostudies-literature | 2012 Apr

REPOSITORIES: biostudies-literature