Homo-Brook route to benzazocenols and congeners via allylsilane-derived aziridines

被引：14
作者：
Ducray, R
Cramer, N
Ciufolini, MA
机构：
[1] Univ Lyon 1, Lab Synth & Methodol Organ, CNRS, UMR 5078, F-69622 Villeurbanne, France
[2] Ecole Super Chim Phys Elect Lyon, F-69622 Villeurbanne, France
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 52期
关键词：
allylsilanes; antitumor agents; azides; aziridines; heterocycles; mitomycinoids;
D O I：
10.1016/S0040-4039(01)02018-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We describe a concise entry to benzazocenols intermediates for mitomycinoids via a homo-Brook rearrangement-ring opening sequence of a silylated aziridine. The latter is obtained by intramolecular 1,3-dipolar cycloaddition of an azide with an allylsilane, followed by irradiation of the resulting triazoline. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：9175 / 9178
页数：4
相关论文
共 26 条
[1]   IMPROVED AMINATION BY ETHYL N-([(4-NITROPHENYL)SULPHONYL]OXY) CARBAMATE IN THE PRESENCE OF INORGANIC OXIDES OR CARBONATES [J].
BARANI, M ;
FIORAVANTI, S ;
LORETO, MA ;
PELLACANI, L ;
TARDELLA, PA .
TETRAHEDRON, 1994, 50 (12) :3829-3834
[2]   A remarkable ene-like reaction: Development and synthetic applications [J].
Ciufolini, MA ;
Deaton, MV ;
Zhu, SR ;
Chen, MY .
TETRAHEDRON, 1997, 53 (48) :16299-16312
[3]   Application of ene-like reactions of aldehydes with vinyl ethers: Facile assembly of benzazocenone intermediates for mitomycinoids [J].
Ciufolini, MA ;
Chen, MY ;
Lovett, DP ;
Deaton, MV .
TETRAHEDRON LETTERS, 1997, 38 (25) :4355-4358
[4]  
DANISHEFSKY SJ, 1995, SYNLETT, P475
[5]   A NEW APPROACH TO THE BICYCLIC HYDROXYLAMINE HEMIKETAL RING-SYSTEM OF ANTITUMOR-ANTIBIOTIC FR900482 VIA OXIDATIVE RING EXPANSION OF A TETRAHYDROPYRROLO[1,2-A]INDOLE [J].
DMITRIENKO, GI ;
DENHART, D ;
MITHANI, S ;
PRASAD, GKB ;
TAYLOR, NJ .
TETRAHEDRON LETTERS, 1992, 33 (39) :5705-5708
[6]  
Ducray R, 2001, Z KRIST-NEW CRYST ST, V216, P347
[7]  
Ducray R, 2001, Z KRIST-NEW CRYST ST, V216, P349
[8]   Application of ring-closing metathesis to the formal total synthesis of (+)-FR900482 [J].
Fellows, IM ;
Kaelin, DE ;
Martin, SF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (44) :10781-10787
[9]   A NOVEL ROUTE TO N-SUBSTITUTED ALLYLAMINES BY THE REACTION OF ALLYLSILANES WITH (ETHOXYCARBONYL)NITRENE [J].
FIORAVANTI, S ;
LORETO, MA ;
PELLACANI, L ;
RAIMONDI, S ;
TARDELLA, PA .
TETRAHEDRON LETTERS, 1993, 34 (25) :4101-4104
[10]   TOTAL SYNTHESIS OF (+/-)-FR-900482 [J].
FUKUYAMA, T ;
XU, LH ;
GOTO, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (01) :383-385
123