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
收藏
页码：12649 / 12652
页数：4
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