Synthesis of azaspiro[4.5]decane systems by oxidative cyclization of olefinic precursors

被引：24

作者：

Martín-López, MJ ^{[1
]}

Bermejo, F ^{[1
]}

机构：

[1] Univ Salamanca, Fac Quim, Dept Quim Organ, E-37008 Salamanca, Spain

来源：

TETRAHEDRON | 1998年 / 54卷 / 40期

关键词：

alkaloids; amino acids and derivatives; spiro compounds; lactones; lactams;

D O I：

10.1016/S0040-4020(98)00746-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 6-benzyloxycarbonyl-1-oxa-6-azaspiro[4,5]decan-2-one (17) and 6-benzyloxycarbonyl-1,6-diazaspiro[4.5]decan-2-one (18) from the D,L-pipecolic acid derivative 10, is described. The synthesis of (+/-)-6-benzyl-3-methyl-1,6-diazaspiro[4.5]dec-3-ene-2,7-dione (29), the spiro structural unit of (+/-)-pandamarine (8) has been achieved by oxidative cylization of the (Z) and (E) isomers of 5-(N-benzyl-4-carboxamidobutylidene)-3-methyl-3-pyrrolin-2-one (25) and (26). The stereoselectivity obtained in the intramolecular cyclization process has also been discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：12379 / 12388

页数：10

共 29 条

[1] ACETYLCHOLINE RECEPTOR AND ION CONDUCTANCE MODULATOR SITES AT MURINE NEUROMUSCULAR JUNCTION - EVIDENCE FROM SPECIFIC TOXIN REACTIONS [J].

ALBUQUER.EX ;

BARNARD, EA ;

CHIU, TH ;

LAPA, AJ ;

DOLLY, JO ;

JANSSON, SE ;

DALY, J ;

WITKOP, B .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1973, 70 (03) :949-953

[2]

Bartlett P.A., 1984, ASYMMETRIC SYNTHESIS, V3, P411

[3]

BUTTERY RG, 1983, CHEM IND-LONDON, P478

[4] THE X-RAY CRYSTAL-STRUCTURE OF (+/-)-PANDAMARINE, THE MAJOR ALKALOID OF PANDANUS-AMARYLLIFOLIUS [J].

BYRNE, LT ;

GUEVARA, BQ ;

PATALINGHUG, WC ;

RECIO, BV ;

UALAT, CR ;

WHITE, AH .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1992, 45 (11) :1903-1908

[5] Pinnaic acid and tauropinnaic acid: Two novel fatty acids composing a 6-Azaspiro[4.5]decane unit from the Okinawan bivalve Pinna muricata [J].

Chou, T ;

Kuramoto, M ;

Otani, Y ;

Shikano, M ;

Yazawa, K ;

Uemura, D .

TETRAHEDRON LETTERS, 1996, 37 (22) :3871-3874

[6]

CORRIE JET, 1971, TETRAHEDRON LETT, V12, P4873

[7] CLASSIFICATION OF SKIN ALKALOIDS FROM NEOTROPICAL POISON-DART FROGS (DENDROBATIDAE) [J].

DALY, JW ;

BROWN, GB ;

MENSAHDWUMAH, M ;

MYERS, CW .

TOXICON, 1978, 16 (02) :163-188

[8] INTERACTIONS OF PERHYDROHISTRIONICOTOXIN WITH POSTSYNAPTIC MEMBRANES [J].

ELLIOTT, J ;

RAFTERY, MA .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1977, 77 (04) :1347-1353

[9]

EVANS DA, 1979, TETRAHEDRON LETT, V20, P411

[10] (E)-3-BENZYLIDENEPHTHALIDES [J].

HOWE, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (24) :4164-4167

← 1 2 3 →