通过非对映选择性的醛醇缩合/β-消除反应序列的对映选择性合成α-亚甲基-β-羟基羧酸衍生物：在 tedanolide C 的 C(15)-C(21)片段中的应用。
Enantioselective synthesis of alpha-methylene-beta-hydroxy carboxylic acid derivatives via a diastereoselective aldol/beta-elimination sequence: application to the C(15)-C(21) fragment of tedanolide C.
机构信息
Department of Chemistry, The Scripps Research Institute, Scripps Florida, 130 Scripps Way, Jupiter, Florida 33458, USA.
出版信息
Org Lett. 2010 May 21;12(10):2342-5. doi: 10.1021/ol1006955.
Abstract
An enantioselective synthesis of alpha-methylene-beta-hydroxy carboxylic acid derivatives via a highly diastereoselective, one-pot syn-aldol and beta-elimination sequence utilizing the chiral beta-(phenylselenyl)propionyl imide 15 is described. This new method, which constitutes an alternative to the Baylis-Hillman reaction, has been applied to the synthesis of the C(15)-C(21) fragment of tedanolide C.
摘要
通过利用手性β-（苯硒基）丙酰亚胺 15 进行高度非对映选择性、一锅法顺-羟醛缩合和β-消除序列，实现了α-亚甲基-β-羟基羧酸衍生物的对映选择性合成。这种新方法构成了 Baylis-Hillman 反应的替代方法，已应用于 tedanolide C 的 C(15)-C(21)片段的合成。
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