Reaction of Donor-Acceptor Cyclobutanes with Indoles: A General Protocol for the Formal Total Synthesis of (±)-Strychnine and the Total Synthesis of (±)-Akuammicine

被引：102

作者：

Feng, Liang-Wen ^{[1
]}

Ren, Hai ^{[1
]}

Xiong, Hu ^{[1
]}

Wang, Pan ^{[1
]}

Wang, Lijia ^{[1
]}

Tang, Yong ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China

[2] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 11期

基金：

中国国家自然科学基金;

关键词：

annulations; cyclobutanes; diastereoselectivity; heterocycles; natural products; ASYMMETRIC TOTAL-SYNTHESIS; 1ST TOTAL-SYNTHESIS; 4+2 CYCLOADDITION; ORGANIC-SYNTHESIS; NATURAL-PRODUCTS; SUBSTITUTED CYCLOPROPANE; STRATEGY; STRYCHNINE; (+/-)-ASPIDOSPERMIDINE; (+/-)-GONIOMITINE;

D O I：

10.1002/anie.201611734

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A ligand-promoted catalytic [4+2] annulation reaction using indole derivatives and donor-acceptor (D-A) cyclobutanes is reported, thus providing an efficient and atom-economical access to versatile cyclohexa-fused indolines with excellent levels of diastereoselectivity and a broad substrate scope. In the presence of a chiral SaBOX ligand, excellent enantioselectivity was realized with up to 94% ee. This novel synthetic method is applied as a general protocol for the total synthesis of (+/-)-akuammicine and the formal total synthesis of (+/-)-strychnine from the same common-core scaffold.

引用

页码：3055 / 3058

页数：4

共 50 条

[21] INOC reaction in alkaloid synthesis - Stereocontrolled formal total synthesis of (+)-pumiliotoxin C
Toyota, M
Asoh, T
Fukumoto, K
HETEROCYCLES, 1997, 45 (01) : 147 - 156
[22] Simple synthesis of racemic pyrrolo[2,3,b]indoles:: Formal total synthesis of (±)-physostigmine
Tsuji, R
Nakagawa, M
Nishida, A
HETEROCYCLES, 2002, 58 : 587 - 593
[23] DONOR-ACCEPTOR INTERACTIONS, LOCALIZATION ENERGY, AND REACTIVITY OF ADDENDS IN REACTION OF DIENE SYNTHESIS
KONOVALOV, AI
DOKLADY AKADEMII NAUK SSSR, 1975, 223 (03): : 613 - 616
[24] Donor-Acceptor Aminocyclobutane Monoesters: Synthesis and Silylium-Catalyzed (4+2) Annulation with Indoles
Robert, Emma G. L.
Pirenne, Vincent
Wodrich, Matthew D.
Waser, Jerome
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (26)
[25] Synthesis of Multisubstituted Silyloxy-based Donor-Acceptor Cyclobutanes by an Acid-Catalyzed [2+2] Cycloaddition
Takasu, Kiyosei
ISRAEL JOURNAL OF CHEMISTRY, 2016, 56 (6-7) : 488 - 498
[26] Catalytic, diastereoselective synthesis of azepino[1,2-a]indoles via formal [5+2] cycloadditions of N-indolyl alkylidene β-amide esters and alkenes: Putative donor-acceptor cyclobutanes as reactive intermediates
Shenje, Raynold
Martin, Maria C.
France, Stefan A.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
[27] Direct approaches to annulated indoles. A formal total synthesis of 0231B
Kraus, GA
Wu, T
TETRAHEDRON, 2005, 61 (40) : 9502 - 9505
[28] Enantioselective total synthesis of (-)-strychnine using the catalytic asymmetric Michael reaction and tandem cyclization
Ohshima, T
Xu, JY
Takita, R
Shimizu, S
Zhong, DF
Shibasaki, M
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (49) : 14546 - 14547
[29] Enantioselective total synthesis of (-)-strychnine using the catalytic asymmetric Michael reaction and tandem cyclization
1600, American Chemical Society (124):
[30] The bromoquinone annulation reaction: a formal total synthesis of EO9
Comer, E
Murphy, WS
ARKIVOC, 2003, : 286 - 296

← 1 2 3 4 5 →