Bioinspired Total Synthesis of Bolivianine: A Diels - Alder/Intramolecular Hetero-Diels-Alder Cascade Approach

被引：100

作者：

Yuan, Changchun ^{[1
]}

Du, Biao ^{[1
]}

Yang, Li ^{[1
]}

Liu, Bo ^{[1
,2
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Sichuan, Peoples R China

[2] Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 25期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; CATALYZED 4+2 CYCLOADDITION; ASYMMETRIC TOTAL-SYNTHESIS; SESQUITERPENE LACTONE; BIOMIMETIC SYNTHESES; BUILDING-BLOCKS; BIOSYNTHESIS; CONCISE; (E)-BETA-OCIMENE; DERIVATIVES;

D O I：

10.1021/ja4040335

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report the first total synthesis of bolivanine in a 14 step pathway involving the synthesis of onoseriolide. Our synthesis features a palladium-catalyzed intramolecular cyclopropanation involving an allylic metal carbene and a Diels-Alder/intramolecular hetero-Diels-Alder cascade, allowing the single-step assembly of a tricyclic system with proper configuration. The synthetic efforts validate our modified biogenetic hypothesis and allow us to confirm the absolute configuration of bolivianine.

引用

页码：9291 / 9294

页数：4

共 54 条

[51] Total Synthesis of (±)-Chloranthalactone A [J].