高效、第二代合成 (+)-桑辛素 A 的特征性二氧杂双环[3.2.1]辛烷核心，并对（Z,Z,E）-三烯酸系统进行了阐述。
An efficient, second-generation synthesis of the signature dioxabicyclo[3.2.1]octane core of (+)-sorangicin A and elaboration of the (Z,Z,E)-triene acid system.
机构信息
Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
出版信息
Org Lett. 2009 Mar 5;11(5):1099-102. doi: 10.1021/ol802942j.
Abstract
An efficient, second-generation synthesis of the signature dioxabicyclo[3.2.1]octane core of (+)-sorangicin A (1), in conjunction with an effective, stereocontrolled protocol to arrive at the requisite (Z,Z,E)-triene acid system has been developed. Highlights of the core construction entail a three-component union, a KHMDS-promoted epoxide ring formation-ring opening cascade, a Takai olefination, and a chemoselective Sharpless dihydroxylation. Assembly of the triene acid system was then achieved via Stille cross-coupling with the ethyl ester of (Z,Z)-5-tributylstannyl-2,4-pentadienoic acid, followed by mild hydrolysis preserving the triene configuration.
摘要
已开发出一种高效、第二代的 (+)-sorangicin A（1）特征性的二环[3.2.1]辛烷核心的合成方法，同时还开发出一种有效、立体控制的方案，以获得所需的（Z，Z，E）-三烯酸系统。核心结构的重点包括三组分结合、KHMDS 促进的环氧化物环形成-开环级联、Takai 烯丙基化以及选择性Sharpless 双羟化。然后通过（Z，Z）-5-三丁基锡基-2,4-戊二烯酸乙酯的 Stille 交叉偶联来组装三烯酸系统，随后进行温和水解以保持三烯构型。
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