Total Synthesis of KingianinsA, D, and F

被引：61
|
作者：
Drew, Samuel L. [1 ]
Lawrence, Andrew L. [1 ]
Sherburn, Michael S. [1 ]
机构：
[1] Australian Natl Univ, Res Sch Chem, Australian Res Council Ctr Excellence Free Rad Ch, Canberra, ACT 0200, Australia
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 15期
基金：
澳大利亚研究理事会;
关键词：
biomimetic synthesis; domino reactions; natural products; polyynes; radical cations; ENDIANDRIC ACID CASCADE; STEREOCONTROLLED TOTAL-SYNTHESIS; BIOMIMETIC SYNTHESIS; ORGANIC-SYNTHESIS; STREPTOMYCES-SPECTABILIS; INTRORSA LAURACEAE; SELECTIVE SYNTHESIS; COUPLING REACTIONS; CARBOXYLIC-ACID; SNF4435C;
D O I：
10.1002/anie.201210084
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A synthesis fit for a king: The total synthesis of (±)-kingianinsA, D, and F has been achieved in ten steps. Key features include the gram-scale synthesis and partial reduction of a conjugated tetrayne to a (Z,Z,Z,Z)-tetraene, the domino 8π-6π electrocyclic ring closure of a (Z,Z,Z,Z)-tetraene, and the radical-cation-catalyzed formal Diels-Alder dimerization of functionalized bicyclo[4.2.0]octadiene precursors. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：4221 / 4224
页数：4
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