（-）-SNF4435 C和（+）-SNF4435 D的全合成。

The total synthesis of (-)-SNF4435 C and (+)-SNF4435 D.

作者信息

Parker Kathlyn A, Lim Yeon-Hee

机构信息

Department of Chemistry, State University of New York at Stony Brook, Stoney Brook, New York 11794-3400, USA.

出版信息

J Am Chem Soc. 2004 Dec 15;126(49):15968-9. doi: 10.1021/ja044733l.

DOI:10.1021/ja044733l

PMID:15584723

Abstract

The size and positioning of substituents on a tetraene, along with the Woodward-Hoffmann rules, control the relative stereochemistry at the four adjacent chiral centers that are generated in the 8pi/6pi electrocyclization cascade. A biomimetic synthesis of (-)-SNF4435 C and (+)-SNF4435 D exploits these steric effects and allows confirmation of the predicted absolute stereochemistry of the natural products.

摘要

四烯上取代基的大小和位置，连同伍德沃德-霍夫曼规则，控制着在8π/6π电环化级联反应中生成的四个相邻手性中心的相对立体化学。（-）-SNF4435 C和（+）-SNF4435 D的仿生合成利用了这些空间效应，并证实了天然产物预测的绝对立体化学。