Enantiospecific synthesis of annulated nicotine analogues from D-Glutamic acid.: 7-azabicyclo[2.2.1]heptano[2.3-c]pyridines

被引：31

作者：

Lennox, JR ^{[1
]}

Turner, SC ^{[1
]}

Rapoport, H ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 21期

关键词：

D O I：

10.1021/jo010534y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The conformationally restricted nicotinoid (1S,4S)-7-methyl-7-azabicyclo[2.2.1]heptano[2,3-c]pyridine dihydrochloride has been prepared enantiospecifically from D-glutamic acid, The method involved a lithium cis-2,6-dimethylpiperidide-mediated intramolecular anionic cyclization of (2S,5R)-N-(tert-butyloxycarbonyl)-5-[3-(4-N-chloropyridinyl]proline methyl ester in tandem with a standard decarboxylation sequence. Reductive amination afforded the desired N-methylated [2.2.1]bicyclonicotinoid. Cyclization of the corresponding iodopyridinylproline methyl ester, obtained via ultrasound-facilitated chloro-iodo exchange, was also effected.

引用

页码：7078 / 7083

页数：6

共 30 条

[1]

[Anonymous], NEURONAL NICOTINIC R

[2]

ARTAMKINA GA, 1990, ZH ORG KHIM+, V26, P225

[3]

BANKS RE, 1988, J CHEM RES SYNOP, V33

[4] Broad-spectrum, non-opioid analgesic activity by selective modulation of neuronal nicotinic acetylcholine receptors [J].

Bannon, AW ;

Decker, MW ;

Holladay, MW ;

Curzon, P ;

Donnelly-Roberts, D ;

Puttfarcken, PS ;

Bitner, RS ;

Diaz, A ;

Dickenson, AH ;

Porsolt, RD ;

Williams, M ;

Arneric, SP .

SCIENCE, 1998, 279 (5347) :77-81

[5] Mono- and disubstituted-3,8-diazabicyclo[3.2.1]octane derivatives as analgesics structurally related to epibatidine: Synthesis, activity, and modeling [J].

Barlocco, D ;

Cignarella, G ;

Tondi, D ;

Vianello, P ;

Villa, S ;

Bartolini, A ;

Ghelardini, C ;

Galeotti, N ;

Anderson, DJ ;

Kuntzweiler, TA ;

Colombo, D ;

Toma, L .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (05) :674-681

[6] SYNTHESIS OF PRIMARY OMEGA-PHENYL-OMEGA-PYRIDYLALKYLAMINES [J].

BUSCHAUER, A .

ARCHIV DER PHARMAZIE, 1989, 322 (03) :165-171

[7] Chirospecific syntheses of conformationally constrained 7-azabicycloheptane amino acids by transannular alkylation [J].

Campbell, JA ;

Rapoport, H .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6313-6325

[8] POLYFLUOROARYL ORGANOMETALLIC COMPOUNDS .17. 2,4,6-TRIS(TRIFLUOROMETHYL)PHENYLLITHIUM, A STERICALLY CROWDED SYSTEM [J].

CARR, GE ;

CHAMBERS, RD ;

HOLMES, TF ;

PARKER, DG .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 325 (1-2) :13-23

[9] DELOCALIZED NITROGEN CARBANIONS IN S(RN)1 REACTIONS [J].

CHAHMA, M ;

COMBELLAS, C ;

THIEBAULT, A .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (24) :8015-8022

[10]

CHAHMA M, 1994, SYNTHESIS-STUTTGART, P366

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