Organocatalytic asymmetric total synthesis of (R)-Rolipram and formal synthesis of (3S,4R)-Paroxetine

被引：130

作者：

Hynes, Peter S. ^{[1
]}

Stupple, Paul A. ^{[2
]}

Dixon, Darren J. ^{[1
]}

机构：

[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

[2] Pfizer Global Res & Dev, Sandwich CT13 9NJ, Kent, England

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 07期

关键词：

D O I：

10.1021/ol800108u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient enantioselective total synthesis of (R)-rolipram and an efficient enantioselective formal synthesis of (3S,4R)-paroxetine has been achieved using the highly enantioselective Michael addition of malonate nucleophiles as key steps in both cases.

引用

页码：1389 / 1391

页数：3

共 55 条

[1] The nitro-Mannich reaction and its application to the stereoselective synthesis of 1,2-diamines [J].

Adams, H ;

Anderson, JC ;

Peace, S ;

Pennell, AMK .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9932-9934

[2]

ALVAREZBUILLA J, 1994, SYNTHESIS-STUTTGART, P559

[3]

[Anonymous], [No title captured]

[4]

[Anonymous], 1975, Patent, Patent No. [US 4012495A, 4012495]

[5]

[Anonymous], [No title captured]

[6] Development of a catalytic enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes for the synthesis of endothelin-A antagonist ABT-546. Scope, mechanism, and further application to the synthesis of the antidepressant rolipram [J].

Barnes, DM ;

Ji, JG ;

Fickes, MG ;

Fitzgerald, MA ;

King, SA ;

Morton, HE ;

Plagge, FA ;

Preskill, M ;

Wagaw, SH ;

Wittenberger, SJ ;

Zhang, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) :13097-13105

[7]

Barnes R. D., 1986, U.S. Patent, Patent No. 24721723

[8] THE CRYSTAL-STRUCTURE, ABSOLUTE-CONFIGURATION, AND PHOSPHODIESTERASE INHIBITORY ACTIVITY OF (+)-1-(4-BROMOBENZYL)-4-(3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL)-PYRROLIDIN-2-ONE [J].

BAURES, PW ;

EGGLESTON, DS ;

ERHARD, KF ;

CIESLINSKI, LB ;

TORPHY, TJ ;

CHRISTENSEN, SB .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (22) :3274-3277

[9] Enantioselective syntheses of (-)-(R)-rolipram, (-)-(R)-baclofen and other GABA analogues via rhodium-catalyzed conjugate addition of arylboronic acids [J].

Becht, JM ;

Meyer, O ;

Helmchen, G .

SYNTHESIS-STUTTGART, 2003, (18) :2805-2810

[10] Enantioselective aza-Henry reaction using cinchona organocatalysts [J].

Bernardi, L ;

Fini, F ;

Herrera, RP ;

Ricci, A ;

Sgarzani, V .

TETRAHEDRON, 2006, 62 (2-3) :375-380

← 1 2 3 4 5 6 →