（11S）-和（11R）-环辛酰胺 A 的全合成。
Total synthesis of nominal (11S)- and (11R)-cyclocinamide A.
机构信息
Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, USA.
出版信息
Org Lett. 2012 Apr 20;14(8):2054-7. doi: 10.1021/ol300576n. Epub 2012 Apr 5.
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.
摘要
环辛酰胺具有独特的β(2)αβ(2)α 14 元四肽核心。最初报道的生物学数据和有趣的结构，由于没有完全的立体化学鉴定，因此需要合成标称（全 S）环辛酰胺 A 和 11R 异构体。该合成的突出特点是使用含有（环）天冬酰胺的二肽作为转角诱导片段。由于天然和合成样品的分析数据不一致，似乎有必要重新评估天然产物的立体化学。
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