氘标记（2S）-环己烯基丙氨酸的立体选择性合成，肉桂酰胺的生物合成中间体。
Stereoselective synthesis of deuterium-labeled (2S)-cyclohexenyl alanines, biosynthetic intermediates of cinnabaramide.
机构信息
Saarland University, Institute of Organic Chemistry, Campus, Bldg. C4.2, D-66123 Saarbruecken, Germany.
出版信息
Org Lett. 2012 Dec 7;14(23):6064-7. doi: 10.1021/ol3029548. Epub 2012 Nov 19.
PMID:23163839
Abstract
Dideuterated β-cyclohexenylalanines, proposed biosynthetic intermediates of the cinnabaramides, can be obtained from chiral alkynols via a sequence of Irland-Claisen rearrangement, ring closing metathesis, and radical decarboxylation. Feeding experiments indicate that both (2S)-β-cyclohexenylalanines can be incorporated into cinnabaramide, while the configuration at the cyclohexenyl ring does not restrict biosynthetic processing.
摘要
氘代β-环己烯基丙氨酸是肉桂酰胺类化合物的生物合成中间体，可通过手性炔醇的爱尔兰-克莱森重排、闭环复分解和自由基脱羧反应序列获得。饲喂实验表明，(2S)-β-环己烯基丙氨酸都可以掺入肉桂酰胺中，而环己烯环的构型并不限制生物合成过程。
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