串联分子内迈克尔-羟醛反应作为构建六环酸C环的工具。

Tandem intramolecular Michael-aldol reaction as a tool for the construction of the C-ring of hexacyclinic acid.

作者信息

Stelmakh Andriy, Stellfeld Timo, Kalesse Markus

机构信息

Institute of Organic Chemistry, University of Hannover, Schneiderberg 1B, 30167 Hannover, Germany.

出版信息

Org Lett. 2006 Aug 3;8(16):3485-8. doi: 10.1021/ol061096q.

DOI:10.1021/ol061096q

PMID:16869641

Abstract

[reaction: see text] The tandem intramolecular Michael-aldol reaction was studied as a tool for the construction of the C-ring of hexacyclinic acid. By changing the reaction conditions it was possible to selectively obtain either the kinetic or the thermodynamic product. Retro-aldol reaction and subsequent epimerization provides four individual cyclopentane derivatives that can be incorporated as building blocks in natural product syntheses.

摘要

[反应：见正文] 串联分子内迈克尔-羟醛反应作为构建六环素酸C环的工具进行了研究。通过改变反应条件，可以选择性地获得动力学产物或热力学产物。逆羟醛反应及随后的差向异构化产生了四种单独的环戊烷衍生物，它们可作为天然产物合成的构建单元。