Enantioselective Total Synthesis of Cerorubenic Acid-III via Type II [5+2] Cycloaddition Reaction

被引：2

作者：

Liu, Xin ^{[1
]}

Liu, Junyang ^{[1
,2
]}

Wu, Jianlei ^{[1
]}

Li, Chuang-Chuang ^{[1
]}

机构：

[1] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Dept Chem,Guangdong Prov Key Lab Catalysis, Shenzhen Key Lab Small Mol Drug Discovery & Synth, Shenzhen 518055, Peoples R China

[2] Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, Shenzhen 518055, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 16期

基金：

中国国家自然科学基金;

关键词：

ANICETUS-BENEFICUS ISHII; HOST SELECTION BEHAVIOR; RUBENS MASKELL HEMIPTERA; YASUMATSU HYMENOPTERA; NATURAL-PRODUCTS; RING-SYSTEMS; CONSTRUCTION; ENCYRTIDAE; STIMULANTS; CLEAVAGE;

D O I：

10.1021/acs.joc.1c00185

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first enantioselective total synthesis of cerorubenic acid-III is described in detail. Different strategies and attempts, based on a type II [5+2] cycloaddition reaction, leading to the bicyclo[4.4.1] ring system with a strained bridgehead double bond, are depicted. Furthermore, sodium naphthalenide was found to be efficient in the chemoselective reduction of 8-oxabicyclo[3.2.1]octene, with three transformations completed in one operation. An unusual S(N)1 transannular cyclization reaction was applied to construct the synthetically challenging vinylcyclopropane moiety. This strategy enabled the total synthesis of cerorubenic acid-III in 19 steps.

引用

页码：11125 / 11139

页数：15

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