手性巴豆基硅烷的对映选择性[4 + 2]环化反应：在白藜芦醇A的C1-C22片段合成中的应用。

Enantioselective [4 + 2]-annulation of chiral crotylsilanes: application to the synthesis of a C1-C22 fragment of leucascandrolide A.

作者信息

Dakin Les A, Panek James S

机构信息

Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.

出版信息

Org Lett. 2003 Oct 16;5(21):3995-8. doi: 10.1021/ol035581m.

DOI:10.1021/ol035581m

PMID:14535762

Abstract

[reaction: see text] The asymmetric synthesis of a C1-C22 fragment (2) of leucascandrolide A is described. Synthetic highlights include the construction of the C9-C22 pyran fragment using a formal [4 + 2]-annulation of a chiral organosilane. A diastereoselctive Mukaiyama aldol was used to introduce the C9 stereocenter and complete the assembly of the macrocycle's carbon skeleton.

摘要

[反应：见正文] 描述了亮叶穿心莲内酯A的C1-C22片段（2）的不对称合成。合成亮点包括使用手性有机硅烷的形式[4 + 2]环化构建C9-C22吡喃片段。采用非对映选择性的木山醇醛反应引入C9立体中心并完成大环碳骨架的组装。