A bioinspired, one-step total synthesis of peshawaraquinone

被引：4
|
作者：
de Castro, Tomas Vieira [1 ,2 ]
Huang, David M. M. [1 ]
Sumby, Christopher J. J. [1 ]
Lawrence, Andrew L. L. [2 ]
George, Jonathan H. H. [1 ]
机构：
[1] Univ Adelaide, Dept Chem, Adelaide, SA 5000, Australia
[2] Univ Edinburgh, EaStCHEM Sch Chem, Joseph Black Bldg,David Brewster Rd, Edinburgh EH9 3FJ, Scotland
来源：
CHEMICAL SCIENCE | 2023年 / 14卷 / 04期
基金：
澳大利亚研究理事会;
关键词：
ACID;
D O I：
10.1039/d2sc05377b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A concise synthesis of a stereochemically complex meroterpenoid, peshawaraquinone, via the unsymmetrical dimerization of its achiral precursor, dehydro-alpha-lapachone, is reported. Enabled by reversible oxa-6 pi-electrocyclizations of 2H-pyran intermediates, the base-catalyzed dimerization sets up an intramolecular (3 + 2) cycloaddition, with the formation of six stereocenters during the cascade. Combining the generation and in situ dimerization of dehydro-alpha-lapachone allows a one-step total synthesis of peshawaraquinone from lawsone and prenal.
引用
收藏
页码：950 / 954
页数：5
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