Total Synthesis of Naphterpin and Marinone Natural Products

被引：20
|
作者：
Murray, Lauren A. M. [1 ]
Fallon, Thomas [1 ]
Sumby, Christopher J. [1 ]
George, Jonathan H. [1 ]
机构：
[1] Univ Adelaide, Dept Chem, Adelaide, SA 5005, Australia
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 20期
基金：
澳大利亚研究理事会;
关键词：
STRUCTURAL ELUCIDATION; BIOMIMETIC SYNTHESIS; NAPHTHOQUINONES; MEROCHLORINS; BIOSYNTHESIS; ANTIBIOTICS;
D O I：
10.1021/acs.orglett.9b03095
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A concise and divergent strategy for the synthesis of the naphterpin and marinone meroterpenoid families has been developed. The approach features a succession of pericyclic reactions-an aromatic Claisen rearrangement, a retro-6 pi-electrocyclization, and two Diels-Alder reactions-which facilitated the first total synthesis of naphterpin itself in five steps from 2,5-dimethoxyphenol, alongside similar syntheses of 7-demethylnaphterpin and debromomarinone. Late-stage oxidation and bromination reactions were also investigated, leading to the first total syntheses of naphterpins B and C and isomarinone.
引用
收藏
页码：8312 / 8315
页数：4
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