(+)-番荔枝辛D的全合成

Total synthesis of (+)-crocacin D.

作者信息

Dias Luiz C, de Oliveira Luciana G, Vilcachagua Janaína D, Nigsch Florian

机构信息

Instituto de Química, Universidade Estadual de Campinas, UNICAMP, C. P. 6154 Campinas, SP, Brazil.

出版信息

J Org Chem. 2005 Mar 18;70(6):2225-34. doi: 10.1021/jo047732k.

DOI:10.1021/jo047732k

PMID:15760209

Abstract

[structure: see text] The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moiety followed by a mild and efficient copper-catalyzed coupling between (+)-crocacin C and a (Z)-vinyl iodide to establish the challenging (Z)-enamide function.

摘要

[结构：见正文] 描述了（+）-番红花酸D的全合成。该汇聚式不对称合成依赖于使用（E）-乙烯基锡烷与（E）-乙烯基碘之间的Stille交叉偶联来构建（E，E）-二烯酰胺部分，随后进行（+）-番红花酸C与（Z）-乙烯基碘之间温和且高效的铜催化偶联以构建具有挑战性的（Z）-烯酰胺官能团。