Asymmetric Total Synthesis of Dankasterones A and B and Periconiastone A Through Radical Cyclization

被引：21

作者：

Chen, Pengquan ^{[1
]}

Wang, Cheng ^{[1
]}

Yang, Rui ^{[1
]}

Xu, Hongjin ^{[1
]}

Wu, Jinghua ^{[1
]}

Jiang, Huanfeng ^{[1
]}

Chen, Kai ^{[2
,3
]}

Ma, Zhiqiang ^{[1
]}

机构：

[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Wushan Rd 381, Guangzhou 510641, Peoples R China

[2] Cent South Univ, Coll Chem & Chem Engn, Changsha 410083, Peoples R China

[3] Peking Univ, Lab Computat Chem & Drug Design, State Key Lab Chem Oncogen, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 10期

基金：

中国国家自然科学基金;

关键词：

cis-decalin; hydrogen atom transfer; radical cyclization; steroids; total synthesis; BEI TERPENOIDEN POLYENVERBINDUNGEN; BIOMIMETIC TOTAL-SYNTHESIS; NATURAL-PRODUCTS; UNACTIVATED OLEFINS; STEREOCHEMISTRY; HYDROAMINATION; HYDROGENATION; MITTEILUNG; REDUCTION; OXIDATION;

D O I：

10.1002/anie.202013881

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We describe herein the assembly of the cis-decalin framework through radical cyclization initiated by metal-catalyzed hydrogen atom transfer (MHAT), further applied it in the asymmetric synthesis of dankasterones A and B and periconiastone A. Position-selective C-H oxygenation allowed for installation of the necessary functionality. A radical rearrangement was adopted to create 13(14 -> 8)abeo-8-ergostane skeleton. Interconversion of dankasterone B and periconiastone A was realized through biomimetic intramolecular aldol and retro-aldol reactions. The MHAT-based approach, serves as a new dissection means, is complementary to the conventional ways to establish cis-decalin framework.

引用

页码：5512 / 5518

页数：7

共 99 条

[91]

Xu, 2017, ANGEW CHEM, V129, P12672

[92] Traversing Biosynthetic Carbocation Landscapes in the Total Synthesis of Andrastin and Terretonin Meroterpenes [J].

Xu, Gong ;

Elkin, Masha ;

Tantillo, Dean J. ;

Newhouse, Timothy R. ;

Maimone, Thomas J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (41) :12498-12502

[93] Total Synthesis of (-)-Daphnezomines A and B [J].

Xu, Guangpeng ;

Wu, Jinbao ;

Li, Luyang ;

Lu, Yunan ;

Li, Chao .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (36) :15240-15245

[94] Enantioselective catalytic approach to the C230-C28 subunit of 24α-methyl steroids [J].

Yakimchyk, Viktoryia S. ;

Kazlova, Volha V. ;

Hurski, Alaksiej L. ;

Savchenko, Rimma G. ;

Kostyleva, Svetlana A. ;

Zhabinskii, Vladimir N. ;

Khripach, Vladimir A. .

STEROIDS, 2019, 148 :82-90

[95] Radicals: Reactive Intermediates with Translational Potential [J].

Yan, Ming ;

Lo, Julian C. ;

Edwards, Jacob T. ;

Baran, Phil S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (39) :12692-12714

[96] A case study in biomimetic total synthesis: Polyolefin carbocyclizations to terpenes and steroids [J].

Yoder, RA ;

Johnston, JN .

CHEMICAL REVIEWS, 2005, 105 (12) :4730-4756

[97] Naturally occurring bioactive 5-ethylidenehydantoins as inspiration for the development of analogues [J].

Yu, Qunying ;

Yu, Jingmou ;

Bao, Haiou ;

Hu, Xiao ;

Ying, Danxia ;

Wu, Lixia ;

Liu, Fang ;

Jiang, Honghong ;

Zhong Jinxia ;

Zhang, Shuihua .

SYNTHETIC COMMUNICATIONS, 2018, 48 (15) :1939-1944

[98]

Zhang B., 2016, ANGEW CHEM, V128, P10591

[99] Total Synthesis of Notoamides F, I, and R and Sclerotiamide [J].

Zhang, Benxiang ;

Zheng, Weifeng ;

Wang, Xiaoqing ;

Sun, Deqian ;

Li, Chaozhong .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (35) :10435-10438

← 1 2 3 4 5 6 7 8 9 10 →