Journal
ORGANIC LETTERS
Volume 14, Issue 8, Pages 2054-2057Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol300576n
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Funding
- NIH IMSD [R25GM58903]
- NIH [R01CA047135]
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The cyclocinamides possess a unique beta(2)alpha beta(2)alpha 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.
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