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

页码：8312 / 8315

页数：4

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