Iodine-Catalyzed Highly Diastereoselective Synthesis of trans-2,6-Disubstituted-3,4-Dihydropyrans: Application to Concise Construction of C28-C37 Bicyclic Core of (+)-Sorangicin A

被引：55

作者：

Mohapatra, Debendra K. ^{[1
]}

Das, Pragna P. ^{[1
]}

Pattanayak, Manas Ranjan ^{[1
,2
]}

Yadav, J. S. ^{[1
]}

机构：

[1] Indian Inst Chem Technol, CSIR, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India

[2] Univ Hyderabad, Indian Inst Chem Technol, Associate Inst, Hyderabad 500046, Andhra Pradesh, India

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 07期

关键词：

asymmetric synthesis; iodine; oxygen heterocycles; sorangicin A; CYTOTOXIC DIMERIC MACROLIDE; MARINE NATURAL-PRODUCTS; SWINHOLIDE-A; MOLECULAR-IODINE; ABSOLUTE STEREOSTRUCTURE; ENANTIOSELECTIVE SYNTHESIS; ACID; DIHYDROPYRANS; DEPROTECTION; OLEFINATION;

D O I：

10.1002/chem.200902999

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel iodine-catalyzed highly diastereoselective synthesis of trans-2,6-disubstituted-3,4-dihydropyrans have been achieved from delta-hydroxy alpha,beta-unsaturated aldehydes by treating with allyltrimethyl silane in THF at room temperature with good to excellent yields. This methodology has been successfully implemented for a concise asymmetric synthesis of C28-C37 dioxabicyclo[3.2.1]octane ring system of (+)-sorangicin A in 8 steps with 21% overall yield

引用

页码：2072 / 2078

页数：7

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