A new approach to isoindolobenzazepines via a ring-expansion of isoindoloisoquinoline:: Synthesis of lennoxamine and chilenine

被引：63

作者：

Koseki, Y ^{[1
]}

Kusano, S ^{[1
]}

Sakata, H ^{[1
]}

Nagasaka, T ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 11期

关键词：

D O I：

10.1016/S0040-4039(99)00140-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient short-step synthesis of lennoxamine 1 and chilenine 2 is described. The key steps are the preparation of an acyliminium ion precursor and a novel expansion of the six-membered ring to a seven-membered ring. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2169 / 2172

页数：4

共 33 条

[1] EPOXIDATION OF VINYLAMIDES BY DIMETHYLDIOXIRANE - FIRST SPECTRAL EVIDENCE FOR ENAMIDE OXIDES [J].

ADAM, W ;

REINHARDT, D ;

REISSIG, HU ;

PAULINI, K .

TETRAHEDRON, 1995, 51 (45) :12257-12262

[2] SYNTHESIS OF ISOINDOLOISOQUINOLINE ALKALOIDS - A REVISION OF THE STRUCTURE OF (+/-)-NUEVAMINE [J].

ALONSO, R ;

CASTEDO, L ;

DOMINGUEZ, D .

TETRAHEDRON LETTERS, 1985, 26 (24) :2925-2928

[3]

BACK TG, 1977, TETRAHEDRON LETT, V31, P2651

[4] ENANTIOMERICALLY PURE PYRUVATE DERIVATIVES BY EPOXIDATION OF YLIDENEDIKETOPIPERAZINES [J].

BARTELS, A ;

JONES, PG ;

LIEBSCHER, J .

TETRAHEDRON LETTERS, 1995, 36 (21) :3673-3674

[5]

BERNHARD HO, 1971, TETRAHEDRON LETT, P4867

[6] The preparation of alpha-substituted, beta-hydroxy piperidines and pyrrolidines: The total synthesis of Febrifugine. [J].

Burgess, LE ;

Gross, EKM ;

Jurka, J .

TETRAHEDRON LETTERS, 1996, 37 (19) :3255-3258

[7] Metalation vs nucleophilic addition in the reactions of N-phenethylimides with organolithium reagents. Ready access to isoquinoline derivatives via N-acyliminium ions and Parham-type cyclizations [J].

Collado, MI ;

Manteca, I ;

Sotomayor, N ;

Villa, MJ ;

Lete, E .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :2080-2092

[8]

DORN CR, 1984, J ORG CHEM, V49, P2642

[9] CHILENINE - AN ISOINDOLOBENZAZEPINE ALKALOID [J].

FAJARDO, V ;

ELANGO, V ;

CASSELS, BK ;

SHAMMA, M .

TETRAHEDRON LETTERS, 1982, 23 (01) :39-42

[10] THE TOTAL SYNTHESIS OF CHILENINE - NOVEL CONSTRUCTIONS OF CYCLIC ENAMIDES [J].

FANG, FG ;

DANISHEFSKY, SJ .

TETRAHEDRON LETTERS, 1989, 30 (21) :2747-2750

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