Tandem Prins-type cyclization for the stereoselective construction of fused polycyclic ring systems†,Organic Chemistry Frontiers

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Tandem Prins-type cyclization for the stereoselective construction of fused polycyclic ring systems†
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2018-02-20 00:00:00 , DOI: 10.1039/c7qo01164d
B. Someswarao _{1,

2,

3,

4,

5} , Rasvan Khan P. _{1,

2,

3,

4} , B. Jagan Mohan Reddy _{2,

3,

4,

5} , Sridhar B. _{4,

6,

7,

8} , V. Subba Reddy B. _{1,

2,

3,

4}

Affiliation

A novel strategy has been developed for the synthesis of fused tetrahydrofuro[3,2-c]pyrano[2,3-b]chromene derivatives through the condensation of 2-hydroxybenzaldehydes with 2-(3,4-dihydro-2H-pyran-5-yl)ethan-1-ol in the presence of 20 mol% TMSOTf in dichloromethane at 25 °C. Similarly, the coupling of aromatic aldehydes with 2-(3,4-dihydro-2H-pyran-5-yl)ethan-1-ol provides the corresponding hexahydro-4H-furo[3′,2′:2,3]indeno[1,2-b]pyran derivatives in good yields with high diastereoselectivity. It is a modular approach for the rapid construction of polycyclic architectures in a single step. These cyclic frameworks are an integral part of the structure of many natural products.

中文翻译：

串联Prins型环化用于稠合多环系统的立体选择性构建†

通过2-羟基苯甲醛与2-（3,4-dihydro-2 H -pyran的缩合反应）合成了稠合的四氢呋喃并[3,2- c ]吡喃并[2,3- b ]色烯衍生物。在25°C下在二氯甲烷中存在20 mol％TMSOTf的情况下生成-5-yl）ethan-1-ol。类似地，芳族醛与2-（3,4-二氢-2 H-吡喃-5-基）乙-1-醇的偶联提供了相应的六氢-4 H-呋喃[3'，2'：2,3 ] indeno [1,2- b ] pyran衍生物，收率高，非对映选择性高。它是一种模块化方法，可在一个步骤中快速构建多环体系结构。这些循环框架是许多天然产物结构的组成部分。

更新日期：2018-02-20

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