Acid-Promoted Cascade Cyclization to Produce 2-(4-Alkoxyaryl)-3,4-Fused Tricyclic Dihydrobenzopyrans via a Vinylidene para-Quinone Methide Intermediate

被引：1

作者：

Choi, Dongil ^{[1
]}

Shiga, Naoki ^{[1
]}

Franzen, Robert ^{[2
]}

Nemoto, Tetsuhiro ^{[1
,3
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan

[2] Univ Turku, Dept Chem, Vatselankatu 2, Turku 20014, Finland

[3] Chiba Univ, Mol Chiral Res Ctr, Inage Ku, 1-33 Yayoi Cho, Chiba 2638522, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 15期

关键词：

Cascade reactions; Dihydrobenzopyrans; Fused-ring systems; Synthetic methods; RECEPTOR-BETA-AGONISTS; ENANTIOSELECTIVE SYNTHESIS; PHENOL DEAROMATIZATION; ASYMMETRIC DEAROMATIZATION; CHROMANS; DERIVATIVES; CYCLOADDITION; CONSTRUCTION; BENZOPYRANS; ALCOHOLS;

D O I：

10.1002/ejoc.201800013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We developed a novel method for synthesizing 2-(4-hydroxyaryl)-3,4-fused tricyclic dihydrobenzopyrans with 2,3-syn and 3,4-syn motif based on the acid-promoted cascade cyclization via vinylidene para-quinone methide intermediates. Using easily prepared linear substrates, TFA-promoted cascade cyclization proceeded in the presence of triethylsilane, affording a series of five to seven-membered ring-fused dihydrobenzopyran derivatives in moderate to excellent yield in a highly diastereoselective manner. The developed method provided new access to potent and selective ER agonists.

引用

页码：1785 / 1788

页数：4