Organocatalytic asymmetric total synthesis of (R)-rolipram and formal synthesis of (3S,4R)-paroxetine.

Organocatalytic asymmetric total synthesis of (R)-rolipram and formal synthesis of (3S,4R)-paroxetine.

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.

Bibliographic Details
Main Authors:	Hynes, P, Stupple, P, Dixon, D
Format:	Journal article
Language:	English
Published:	2008

Similar Items

Asymmetric total synthesis of (−)-(3R)-inthomycin C
by: Balcells, S, et al.
Published: (2018)

Organocatalytic diastereo- and enantioselective Michael addition reactions of 5-aryl-1,3-dioxolan-4-ones.
by: Hynes, P, et al.
Published: (2007)

Organocatalytic asymmetric mannich, formal [4+1] and [4+2] annulation reactions
by: Shi, Zugui
Published: (2012)

Asymmetric synthesis of (-)-(R)-sitagliptin
by: Davies, S, et al.
Published: (2012)

Asymmetric synthesis of (-)-(R)-sitagliptin
by: Davies, S, et al.
Published: (2012)

Asymmetric synthesis of (-)-(R)-sitagliptin
by: Davies, S, et al.
Published: (2012)

Asymmetric synthesis of (4R,5R)-cytoxazone and (4R,5S)-epi-cytoxazone.
by: Davies, S, et al.
Published: (2004)

Asymmetric synthesis of (R)-sulcatol
by: Davies, S, et al.
Published: (1996)

A FORMAL TOTAL ASYMMETRIC-SYNTHESIS OF (+)-THIENAMYCIN
by: Davies, S, et al.
Published: (1995)

Asymmetric organocatalytic relay cascades: catalyst-controlled stereoisomer selection in the synthesis of functionalized cyclohexanes.
by: Wang, Y, et al.
Published: (2009)

Organocatalytic asymmetric 1,3-dipolarand formal 1,3-dipolar cycloaddition reactions.
by: Wang, Fei
Published: (2014)

Concise, efficient and highly selective asymmetric synthesis of (+)-(3S,4R)-cisapride
by: Davies, S, et al.
Published: (2011)

Concise, efficient and highly selective asymmetric synthesis of (+)-(3S,4R)-cisapride
by: Davies, S, et al.
Published: (2011)

A new organocatalytic desymmetrization reaction enables the enantioselective total synthesis of madangamine E
by: Shiomi, S, et al.
Published: (2022)

The asymmetric synthesis of (2R,3R)- and (2R,3S)-3-methyl-aspartates via an enantiodiscrimination strategy
by: Bull, S, et al.
Published: (2001)

Diastereodivergent organocatalytic asymmetric vinylogous Michael reactions
by: Li, X, et al.
Published: (2014)

ORGN 619-Organocatalytic approach to tetrahydrofurans: Application to the total synthesis of (-)-Goniothalesdiol
by: Silva, F, et al.
Published: (2007)

Development of organocatalytic asymmetric a-aminoxylation reactions: enantioselecitve synthesis of oxygenated compounds.
by: Lu, Min
Published: (2014)

Asymmetric synthesis of (-)-(1R,7aS)-absouline
by: Davies, S, et al.
Published: (2013)

Asymmetric synthesis of (-)-(1R,7aS)-absouline
by: Davies, S, et al.
Published: (2013)

Synthesis of (2S,3R,4S),(2S,3S,4R)-epoxyprolines and aminohydroxyprolines
by: Robinson, J, et al.
Published: (1998)

SYNTHESIS OF 2R,3S,4R-DIHYDROXYPROLINE FROM D-RIBONOLACTONE
by: Dho, J, et al.
Published: (1986)

Asymmetric syntheses of 3,4-syn- and 3,4-anti-3-substituted-4- aminopiperidin-2-ones: Application to the asymmetric synthesis of (+)-(3S,4R)-cisapride
by: Davies, S, et al.
Published: (2012)

Asymmetric syntheses of 3,4-syn- and 3,4-anti-3-substituted-4-aminopiperidin-2-ones: application to the asymmetric synthesis of (+)-(3S,4R)-cisapride
by: Davies, S, et al.
Published: (2012)

AN EXPEDITIOUS ASYMMETRIC-SYNTHESIS OF (-)-(1R,2S)-CISPENTACIN
by: Davies, S, et al.
Published: (1993)

Asymmetric synthesis of anti-(2S,3S)- and syn-(2R,3S)-diaminobutanoic acid.
by: Bunnage, M, et al.
Published: (2003)

Absolute configuration assignment by asymmetric syntheses of the homalium alkaloids (-)-(R,R,R)-hoprominol and (-)-(4'S,4″R,2‴R)-hopromalinol.
by: Davies, S, et al.
Published: (2012)

An organocatalytic oxidative coupling strategy for the direct synthesis of arylated quaternary stereogenic centers.
by: Bogle, K, et al.
Published: (2007)

THE SYNTHESIS OF POLYHYDROXYLATED AMINO-ACIDS FROM GLUCURONOLACTONE - ENANTIOSPECIFIC SYNTHESES OF 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2R,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID AND 2R,3R,4R-DIHYDROXYPROLINE
by: Bashyal, B, et al.
Published: (1987)

Asymmetric synthesis of (1R,2S,3R)-gamma-methyl-cis-pentacin by a kinetic resolution protocol.
by: Bailey, S, et al.
Published: (2002)

ASYMMETRIC-SYNTHESIS OF THE N-TERMINAL COMPONENT OF MICROGININ - (2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID, ITS (2R,3R)-EPIMER AND (3R)-3-AMINODECANOIC ACID
by: Bunnage, M, et al.
Published: (1995)

Asymmetric synthesis of (2R,5R)-2,5-diaminohexan-1,6-dioic acid
by: Bull, S, et al.
Published: (1998)

(-)-(2S,3R,Z)-Nakinadine A: first asymmetric synthesis and absolute configuration assignment.
by: Davies, S, et al.
Published: (2014)

Preparation of desymmetrised meso-tartrate derivatives - synthesis and utility of (R ',R ',R,S)-2,3-butane diacetal protected dimethyl tartrate
by: Dixon, D, et al.
Published: (1999)

Asymmetric synthesis of cytotoxic sponge metabolites R-strongylodiols A and B
by: Kirkham, J, et al.
Published: (2004)

Asymmetric synthesis of (1R,2S,3R)-3-methylcispentacin and (1S,2S,3R)-3-methyltranspentacin by kinetic resolution of tert-butyl (+/-)-3-methylcyclopentene-1-carboxylate.
by: Bunnage, M, et al.
Published: (2003)

A short stereoselective synthesis of (R)-salmeterol
by: Buchanan, D, et al.
Published: (2005)

Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives.
by: Ye, J, et al.
Published: (2005)

A PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND OF (2S, 3R, 4R, 5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID FROM D-GLUCOSE
by: Fleet, G, et al.
Published: (1989)

Organocatalytic asymmetric Mannich reactions of 5H-oxazol-4-ones : highly enantio- and diastereoselective synthesis of chiral α-alkylisoserine derivatives
by: Han, Zhiqiang, et al.
Published: (2014)