Total Synthesis of Maoecrystal V

被引：14

作者：

Zhang, Wei-Bin ^{[1
]}

Lin, Guang ^{[1
]}

Shao, Wen-Bin ^{[1
]}

Gong, Jian-Xian ^{[1
]}

Yang, Zhen ^{[1
,2
,3
,4
]}

机构：

[1] Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China

[2] Peking Univ, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China

[3] Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China

[4] Ocean Univ China, Sch Med & Pharm, Chinese Minist Educ, Key Lab Marine Drugs, Qingdao, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2015年 / 10卷 / 04期

基金：

中国博士后科学基金;

关键词：

Diels-Alder reaction; natural products; rhodium; total synthesis; oxidative dearomatization; INTRAMOLECULAR HYDROGEN ABSTRACTION; ORGANIC-SYNTHESIS; REDUCTION; EFFICIENT; DITERPENOIDS; COMPLEX; CORE; DIAZOCARBONYL; REAGENTS; KETONES;

D O I：

10.1002/asia.201403228

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Maoecrystal V (1) is a novel diterpenoid, which was originally isolated from the leaves of the Chinese medicinal herb Isodon eriocalyx in 2004 by Sun etal.1 It has been found to be selectively cytotoxic towards HeLa cells, with an IC50 value of 20ngmL(-1). Significant research efforts have been devoted to the synthesis of maoecrystal V because of its intriguing biological properties, rarity in nature, and complex structural features. Herein, we describe our recent investigations, which have culminated in the total synthesis of (+/-)-maoecrystal V. The current strategy involved three key steps for the successful construction of the key tetrahydrofuran oxa-bridge skeleton, including a Wessely oxidative dearomatization, a novel intramolecular Diels-Alder reaction, and a Rh-II-catalyzed OH insertion reaction.

引用

页码：903 / 909

页数：7

共 69 条

[1] Toward the Total Synthesis of Maoecrystal V: Establishment of Contiguous Quaternary Stereocenters [J].