Auxiliary-controlled stereoselective enolate protonation: Enantioselective synthesis of cis and trans annulated decahydroquinoline alkaloids

被引：33

作者：

Weymann, M ^{[1
]}

Schultz-Kukula, M ^{[1
]}

Kunz, H ^{[1
]}

机构：

[1] Univ Mainz, Inst Organ Chem, D-55099 Mainz, Germany

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 43期

关键词：

D O I：

10.1016/S0040-4039(98)01745-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereoselective synthesis of the octahydroquinoline enone precursor of pumiliotoxin C is achieved via tandem Mannich-Michael reaction on N-galactosyl imines. Conjugate cuprate addition to the bicyclic enone stereoselectively forms the trans annulated 4a-epi-pumiliotoxin C skeleton in the presence of the carbohydrate auxiliary, and the cis annulated pumiliotoxin C skeleton in its absence. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：7835 / 7838

页数：4

相关论文

共 15 条

[1] ASYMMETRIC-SYNTHESIS .8. BIOGENETICALLY PATTERNED APPROACH TO THE CHIRAL TOTAL SYNTHESIS OF (-)-PUMILIOTOXIN-C [J].

BONIN, M ;

ROYER, J ;

GRIERSON, DS ;

HUSSON, HP .

TETRAHEDRON LETTERS, 1986, 27 (14) :1569-1572

[2] ENANTIOPURE N-ACYLDIHYDROPYRIDONES AS SYNTHETIC INTERMEDIATES - THE FIRST ASYMMETRIC-SYNTHESIS OF TRANS-DECAHYDROQUINOLINE ALKALOID-(+)-219A [J].

COMINS, DL ;

DEHGHANI, A .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (04) :794-795

[3]

COMINS DL, 1993, J CHEM SOC CHEM COMM, P18839

[4] DECAHYDROQUINOLINE ALKALOIDS - NONCOMPETITIVE BLOCKERS FOR NICOTINIC ACETYLCHOLINE RECEPTOR-CHANNELS IN PHEOCHROMOCYTOMA CELLS AND TORPEDO ELECTROPLAX [J].

DALY, JW ;

NISHIZAWA, Y ;

PADGETT, WL ;

TOKUYAMA, T ;

MCCLOSKEY, PJ ;

WAYKOLE, L ;

SCHULTZ, AG ;

ARONSTAM, RS .

NEUROCHEMICAL RESEARCH, 1991, 16 (11) :1207-1212

[5]

DALY JW, 1969, LIEBIGS ANN CHEM, V729, P198

[6]

KUNZ H, 1991, SYNTHESIS-STUTTGART, P1039

[7]

KUNZ H, 1989, ANGEW CHEM, V101, P1041

[8] RUTHENIUM-CATALYZED HYDRATION OF NITRILES AND TRANSFORMATION OF DELTA-KETONITRILES TO ENE-LACTAMS - TOTAL SYNTHESIS OF (-)-PUMILIOTOXIN-C [J].

MURAHASHI, SI ;

SASAO, S ;

SAITO, E ;

NAOTA, T .

TETRAHEDRON, 1993, 49 (39) :8805-8826

[9] TOTAL SYNTHESIS OF (-)-PUMILIOTOXIN-C BY AQUEOUS INTRAMOLECULAR ACYLNITROSO DIELS-ALDER APPROACH [J].

NARUSE, M ;

AOYAGI, S ;

KIBAYASHI, C .

TETRAHEDRON LETTERS, 1994, 35 (49) :9213-9216

[10] ENANTIOSELECTIVE SYNTHESIS AND ABSOLUTE-CONFIGURATION OF NATURAL PUMILIOTOXIN-C [J].

OPPOLZER, W ;

FLASKAMP, E .

HELVETICA CHIMICA ACTA, 1977, 60 (01) :204-207