Bioinspired Total Synthesis of Hyperireflexolides A and B

被引：10

作者：

zur Bonsen, Andreas B. ^{[1
]}

Sumby, Christopher J. ^{[1
]}

George, Jonathan H. ^{[1
]}

机构：

[1] Univ Adelaide, Dept Chem, Adelaide, SA 5005, Australia

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 34期

基金：

澳大利亚研究理事会;

关键词：

BIOMIMETIC TOTAL-SYNTHESIS; BETA-DICARBONYL COMPOUNDS; NATURAL-PRODUCTS; ENE REACTIONS; DEAROMATIZATION STRATEGIES; DIKETONES; EFFICIENT; LACTONES; ACCESS;

D O I：

10.1021/acs.orglett.3c02232

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hyperireflexolides A and B were synthesized in six stepsvia thedearomatization and fragmentation of a simple acylphloroglucinol startingmaterial. The dearomatized acylphloroglucinol undergoes a sequenceof oxidative radical cyclization, retro-Dieckmann fragmentation, stereodivergentintramolecular carbonyl-ene reactions, and final & alpha;-hydroxy-& beta;-diketonerearrangements to give the target natural products. This sequenceis based on a biosynthetic proposal that claims the hyperireflexolidesas highly rearranged polycyclic polyprenylated acylphloroglucinols(PPAPs), which is supported by the structural revision of hyperireflexolideB.

引用

页码：6317 / 6321

页数：5

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