Total synthesis of (±)-cytisine

被引：72

作者：

O'Neill, BT ^{[1
]}

Yohannes, D ^{[1
]}

Bundesmann, MW ^{[1
]}

Arnold, EP ^{[1
]}

机构：

[1] Pfizer Inc, Pfizer Global Res & Dev, Groton, CT 06340 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 26期

关键词：

D O I：

10.1021/ol0067538

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The nicotine partial agonist cytisine was prepared in five steps featuring an "in situ" Stille or Suzuki biaryl pyridine coupling. Differentiation of the pyridyl rings was accomplished via selective benzylation and then reduction of a pyridinium ring. The penultimate diazabicyclo[3.3.1]nonane intermediate was obtained with high diastereoselectivity. A similar sequence has been employed for the synthesis of novel derivative 9-methoxycytisine.

引用

页码：4201 / 4204

页数：4

共 29 条

[1] A modified in situ Suzuki cross-coupling of haloarenes for the preparation of C-2-symmetric biaryls
Andersen, NG
Maddaford, SP
Keay, BA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) : 9556 - 9559
[2] NICOTINIC RECEPTOR-BINDING OF [H-3] CYTISINE, [H-3] NICOTINE AND [H-3] METHYLCARBAMYLCHOLINE IN RAT-BRAIN
ANDERSON, DJ
ARNERIC, SP
[J]. EUROPEAN JOURNAL OF PHARMACOLOGY, 1994, 253 (03) : 261 - 267
[3] Palladium/P,O-ligand-catalyzed Suzuki cross-coupling reactions of arylboronic acids and aryl chlorides. Isolation and structural characterization of (P,O)-Pd(dba) complex
Bei, XH
Turner, HW
Weinberg, WH
Guram, AS
Petersen, JL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) : 6797 - 6803
[4] SYNTHESE DES CYTISINS
BOHLMANN, F
ENGLISCH, A
OTTAWA, N
SANDER, H
WEISE, W
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1955, 67 (22) : 708 - 708
[5] Brioni J D, 1997, Adv Pharmacol, V37, P153
[6] A PALLADIUM CATALYZED CROSS-COUPLING BETWEEN FURYLBORATES (GENERATED INSITU) AND ORGANOHALIDES
CRISTOFOLI, WA
KEAY, BA
[J]. TETRAHEDRON LETTERS, 1991, 32 (42) : 5881 - 5884
[7] DEHMLOW EV, 1992, LIEBIGS ANN CHEM, P953
[8] EMBER LR, 1994, CHEM ENG NEWS 1128, P8
[9] SYNTHESIS OF (+/-)-CYTISINE
GOVINDACHARI, TR
RAJADURAI, S
SUBRAMANIAN, M
THYAGARAJAN, BS
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1957, (SEP): : 3839 - 3844
[10] SELECTIVITY IN PALLADIUM(0)-CATALYZED CROSS-COUPLING REACTIONS - APPLICATION TO A TANDEM STILLE REACTION
HITCHCOCK, SA
MAYHUGH, DR
GREGORY, GS
[J]. TETRAHEDRON LETTERS, 1995, 36 (50) : 9085 - 9088

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