Enantioselective synthesis of nicotinic receptor probe 7,8-difluoro-1,2,3,4,5,6-hexahydro-1,5-methano-3-benzazocine

被引：19

作者：

Bashore, Crystal G. ^{[1
]}

Vetelino, Michael G. ^{[1
]}

Wirtz, Michael C. ^{[1
]}

Brooks, Paige R. ^{[1
]}

Frost, Heather N. ^{[1
]}

McDermott, Ruth E. ^{[1
]}

Whritenour, David C. ^{[1
]}

Ragan, John A. ^{[1
]}

Rutherford, Jennifer L. ^{[1
]}

Makowski, Teresa W. ^{[1
]}

Brenek, Steven J. ^{[1
]}

Coe, Jotham W. ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 26期

关键词：

D O I：

10.1021/ol0623062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The development of a concise enantioselective synthesis of nicotinic alkaloid 1 is presented. The route features the synthesis and use of a "stable" aliphatic triflate 21 in an alkylation step to generate Heck precursor 24 and an enantioselective cyclization to establish a compound with the key [ 3.2.1]- bicyclic core, 29.

引用

页码：5947 / 5950

页数：4

共 15 条

[1] Twisted amide reduction under Wolff-Kishner conditions: Synthesis of a benzo-1-aza-adamantane derivative [J].

Bashore, CG ;

Samardjiev, IJ ;

Bordner, J ;

Coe, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (11) :3268-3272

[2] Boron trichloride/tetra-n-butylammonium iodide:: A mild, selective combination reagent for the cleavage of primary alkyl aryl ethers [J].

Brooks, PR ;

Wirtz, MC ;

Vetelino, MG ;

Rescek, DM ;

Woodworth, GF ;

Morgan, BP ;

Coe, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (26) :9719-9721

[3] Design of Ligands for the nicotinic acetylcholine receptors: The quest for selectivity [J].

Bunnelle, WH ;

Dart, MJ ;

Schrimpf, MR .

CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2004, 4 (03) :299-334

[4] In pursuit of α4β2 nicotinic receptor partial agonists for smoking cessation:: Carbon analogs of (-)-cytisine [J].

Coe, JW ;

Vetelino, MG ;

Bashore, CG ;

Wirtz, MC ;

Brooks, PR ;

Arnold, EP ;

Lebel, LA ;

Fox, CB ;

Sands, SB ;

Davis, TI ;

Schulz, DW ;

Rollema, H ;

Tingley, FD ;

O'Neill, BT .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (12) :2974-2979

[5]

COE JW, 1999, Patent No. 9955680

[6] IMPROVED SELECTIVITY IN THE PREPARATION OF SOME 1,1-DIFUNCTIONALIZED 3-CYCLOPENTENES - HIGH-YIELD SYNTHESIS OF 3-CYCLOPENTENECARBOXYLIC ACID [J].

DEPRES, JP ;

GREENE, AE .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (05) :928-931

[7]

DEPRES JP, 1997, ORG SYNTH, V75, P195

[8]

GLENNON RA, 1996, MED CHEM RES, P465

[9]

HAYAN SE, 1991, J MED CHEM, V34, P1155

[10] Neuronal nicotinic acetylcholine receptors as targets for drug discovery [J].

Holladay, MW ;

Dart, MJ ;

Lynch, JK .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (26) :4169-4194

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