Total Synthesis and Structural Revision of Laurefurenynes A and B

被引：32

作者：

Holmes, Michael T. ^{[1
]}

Britton, Robert ^{[1
]}

机构：

[1] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 38期

基金：

加拿大自然科学与工程研究理事会;

关键词：

chlorohydrin; laurefurenyne A; laurencia acetogenins; organocatalysis; total synthesis; ASYMMETRIC ALPHA-CHLORINATION; VERSATILE BUILDING-BLOCKS; MARINE NATURAL-PRODUCTS; RED ALGA; STEREOSELECTIVE-SYNTHESIS; ELATENYNE; TRANSFORMATION; CYCLIZATION; PREDICTION; ETHERS;

D O I：

10.1002/chem.201302352

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Structural reassignment: A total synthesis of the proposed structure of (-)-laurefurenynea A has been accomplished that relies on organocatalytic aldehyde α-chlorination and a flexible chlorohydrin-based strategy for stereocontrolled access to the bis-tetrahydrofuran core of the natural product. Analysis of incongruities between the 1Ha NMR spectra of synthetic and natural material led to a configurational reassignment for the natural product, which was also confirmed by total synthesis. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：12649 / 12652

页数：4

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