文献类型：期刊文献

英文题名：Construction of Chiral Bridged Tricyclic Benzopyrans: Enantioselective Catalytic Diels-Alder Reaction and a One-Pot Reduction/Acid-Catalyzed Stereoselective Cyclization

作者：Song, Aiguo[1];Zhang, Xinshuai[1];Song, Xixi[1];Chen, Xiaobei[1];Yu, Chenguang[1];Huang, He[1];Li, Hao[2,3];Wang, Wei[1,2,3]

机构：[1]Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA;[2]E China Univ Sci & Technol, State Key Lab Bioreactor Engn, Shanghai 200237, Peoples R China;[3]E China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China

年份：2014

卷号：53

期号：19

起止页码：4940

外文期刊名：ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

收录：;EI(收录号：20142017712259);WOS:【SCI-EXPANDED(收录号:WOS:000335202700033)，CCR-EXPANDED(收录号:WOS:000335202700033)】；

基金：Financial support from the NSF (CHE-1057569) and the National Science Foundation of China (No. 21372073) is gratefully acknowledged.

语种：英文

外文关键词：cyclization; decarboxylation; heterocycles; organocatalysis; synthetic methods

摘要：An asymmetric two-step approach to chiral bridged tricyclic benzopyrans, core structures featured in various natural products, is described. In the synthesis, an unprecedented enantioselective catalytic decarboxylative Diels-Alder reaction is developed using readily available coumarin-3-carboxylic acids and aldehydes as reactants under mild reaction conditions. Notably, the decarboxylation-assisted release of the catalyst enables the process to proceed efficiently with high enantio- and diastereoselectivity. Furthermore, a one-pot procedure for either a LiAlH4- or NaBH4-mediated reduction with subsequent acid-catalyzed intramolecular cyclization of the Diels-Alder adducts was identified for the efficient formation of the chiral bridged tricyclic benzopyrans.