The applications of catalytic asymmetric halocyclization in natural product synthesis

被引：26
作者：
Yan, Jiahang [1 ]
Zhou, Zhiqiang [1 ]
He, Qiaoqiao [1 ]
Chen, Guzhou [1 ]
Wei, Hongbo [1 ]
Xie, Weiqing [1 ,2 ]
机构：
[1] Northwest A&F Univ, Coll Chem & Pharm, Shaanxi Key Lab Nat Prod & Chem Biol, 22 Xinong Rd, Yangling 712100, Shaanxi, Peoples R China
[2] Key Lab Bot Pesticide R&D Shaanxi Prov, Yangling 712100, Shaanxi, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 02期
基金：
中国国家自然科学基金;
关键词：
ENANTIOSELECTIVE TOTAL-SYNTHESIS; HALONIUM ION FORMATION; STABLE CARBONIUM-IONS; POLAR ADDITIONS; 2-BUTENE SYSTEMS; ELECTROPHILIC BROMINATION; ALPHA-CHLORINATION; BROMONIUM ION; STRATEGIES; BROMOCYCLIZATION;
D O I：
10.1039/d1qo01395e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Halocyclization of olefinic substrate enables the establishment of cyclic skeletons via intramolecular halonium-induced nucleophilic addition, which has been well utilized as a practical strategy for constructing cyclic skeletons in natural product synthesis. Recently, the renaissance and rapid evolution of organocatalysis have accelerated the development of catalytic asymmetric halocyclization. In this context, natural product synthesis powered by catalytic asymmetric halocyclization has also achieved considerable progress in recent years. In some cases, these newly developed protocols enable more concise synthetic routes for accessing enantioenriched natural products. To this end, this review summarizes the applications of catalytic asymmetric halocyclization in natural product synthesis.
引用
收藏
页码：499 / 516
页数：18
相关论文
共 230 条
[11]   Enantioselective Organocatalyzed Bromolactonizations: Applications in Natural Product Synthesis [J].
Aursnes, Marius ;
Tungen, Jom E. ;
Hansen, Trond V. .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (18) :8287-8295
[12]   Thiourea-Catalyzed Enantioselective Malonate Addition onto 3-Sulfonyl-3′-indolyl-2-oxindoles: Formal Total Syntheses of (-)-Chimonanthine, (-)-Folicanthine, and (+)-Calycanthine [J].
Babu, K. Naresh ;
Roy, Avishek ;
Singh, Manvendra ;
Bisai, Alakesh .
ORGANIC LETTERS, 2018, 20 (20) :6327-6331
[13]   Catalytic, Diastereoselective 1,2-Difluorination of Alkenes [J].
Banik, Steven M. ;
Medley, Jonathan William ;
Jacobsen, Eric N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (15) :5000-5003
[14]   Intramolecular arylation reactions of alkenes:: A flexible approach to chromans and tetrahydroquinoline derivatives [J].
Barluenga, J ;
Trincado, M ;
Rubio, E ;
González, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) :3416-3417
[15]   THE SOLUTION BEHAVIOR OF THE ADAMANTYLIDENEADAMANTANE BROMINE SYSTEM - EXISTENCE OF EQUILIBRIUM MIXTURES OF BROMONIUM POLYBROMIDE SALTS AND A STRONG 1-1 MOLECULAR CHARGE-TRANSFER COMPLEX [J].
BELLUCCI, G ;
BIANCHINI, R ;
CHIAPPE, C ;
MARIONI, F ;
AMBROSETTI, R ;
BROWN, RS ;
SLEBOCKATILK, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) :2640-2647
[16]   AN UNPRECEDENTED RAPID AND DIRECT BR+ TRANSFER FROM THE BROMONIUM ION OF ADAMANTYLIDENEADAMANTANE TO ACCEPTOR OLEFINS [J].
BENNET, AJ ;
BROWN, RS ;
MCCLUNG, RED ;
KLOBUKOWSKI, M ;
AARTS, GHM ;
SANTARSIERO, BD ;
BELLUCCI, G ;
BIANCHINI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8532-8534
[17]   The lyconadins: Enantioselective total syntheses of (+)-lyconadin A and (-)-lyconadin B [J].
Beshore, Douglas C. ;
Smith, Amos B., III .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (41) :13778-13789
[18]   Total syntheses of (+)-lyconadin A and (-)-lyconadin B [J].
Beshore, Douglas C. ;
Smith, Amos B., III .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (14) :4148-+
[19]   POTENT SEX ATTRACTANT OF GYPSY MOTH - ITS ISOLATION, IDENTIFICATION, AND SYNTHESIS [J].
BIERL, BA ;
BEROZA, M ;
COLLIER, CW .
SCIENCE, 1970, 170 (3953) :87-+
[20]   Marine natural products [J].
Blunt, John W. ;
Copp, Brent R. ;
Keyzers, Robert A. ;
Munro, Murray H. G. ;
Prinsep, Michele R. .
NATURAL PRODUCT REPORTS, 2016, 33 (03) :382-431
12345678910