Epoxide-initiated electrophilic cyclization of azides:: A novel route for the stereloselective construction of azabicyclic ring systems and total synthesis of (±)-indolizidine 167B and 209D

被引：60

作者：

Reddy, PG ^{[1
]}

Varghese, B ^{[1
]}

Baskaran, S ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 04期

关键词：

D O I：

10.1021/ol027563v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A novel and general method for the stereoselective construction of 5-hydroxymethyl azabicyclic ring skeletons based on epoxide initiated electrophilic cyclization of azides has been developed and applied in the synthesis of (+/-)-indolizidine 167B and 209D with an overall yield of 16.5% and 17.8%, respectively. The efficiency of this methodology is further exemplified in the synthesis of azepine skeleton via tandem cation-olefin-azide cyclization.

引用

页码：583 / 585

页数：3

共 11 条

[1] Epoxide-initiated cationic cyclization of azides: A novel method for the stereoselective construction of 5-hydroxymethyl azabicyclic compounds and application in the stereo- and enantioselective total synthesis of (+)- and (-)-indolizidine 167B and 209D
Reddy, PG
Baskaran, S
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09): : 3093 - 3101
[2] ENANTIOSELECTIVE TOTAL SYNTHESES OF INDOLIZIDINE ALKALOIDS 167B AND 209D
POLNIASZEK, RP
BELMONT, SE
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15): : 4688 - 4693
[3] ENANTIOSELECTIVE TOTAL SYNTHESES OF INDOLIZIDINE ALKALOIDS 167B AND 209D
POLNIASZEK, RP
BELMONT, SE
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 199 : 27 - ORGN
[4] Arylation of Cyclopropanol with Pyrrole: Asymmetric Synthesis of Indolizidine 167B, Indolizidine 209D, and Monomorine I
Liu, Shuangwei
Su, Xiaojiao
Jiang, Dan
Xiong, Hongbing
Miao, Dingyin
Fu, Lin
Qiu, Hanyue
He, Ling
Zhang, Min
ORGANIC LETTERS, 2023, 25 (12) : 2058 - 2062
[5] Radical cyclization of beta-aminoacrylates: Stereoselective synthesis of indolizidines 167B and 209D
Lee, E
Li, KS
Lim, JH
TETRAHEDRON LETTERS, 1996, 37 (09) : 1445 - 1446
[6] Stereoselective synthesis of C-6 substituted pipecolic acid derivatives. Formal synthesis of (+)-indolizidine 167B and (+)-indolizidine 209D
Carbonnel, S
Troin, Y
HETEROCYCLES, 2002, 57 (10) : 1807 - 1830
[7] Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza Prins reaction of endocyclic N-acyliminium ions: application to the total synthesis of (±)-epi-indolizidine 167B and 209D
Saikia, Anil K.
Indukuri, Kiran
Das, Jagadish
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (36) : 7026 - 7035
[8] Concise syntheses of substituted indolizidine alkaloids via cyclization based on α-sulfinyl carbanions:: preparation of (±)-indolizidines 167B and 209D, their epimers, and (±)-tashiromine
Pohmakotr, Manat
Prateeptongkum, Saisuree
Chooprayoon, Soontorn
Tuchinda, Patoomratana
Reutrakul, Vichai
TETRAHEDRON, 2008, 64 (10) : 2339 - 2347
[9] Convenient new route to piperidines, pyrrolizidines, indolizidines, and quinolizidines by cyclization of acetylenic sulfones with β- and γ-chloroamines.: Enantioselective total synthesis of indolizidines (-)-167B, (-)-209D, (-)-209B, and (-)-207A
Back, TG
Nakajima, K
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15): : 4543 - 4552
[10] [2,3]-Wittig rearrangement approach to iminosugar C-glycosides: 5-epi-ethylfagomine, 2-epi-5-deoxyadenophorine and formal synthesis of indolizidine 167B and 209D
Chandrasekhar, B.
Rao, J. Prasada
Rao, B. Venkateswara
Naresh, P.
TETRAHEDRON LETTERS, 2011, 52 (45) : 5921 - 5925

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