Enzymatic resolution of a key stereochemical intermediate for the synthesis of (-)-taxol

Carl R. Johnson; Yanping Xu; K. C. Nicolaou; Zhen Yang; Rodney K. Guy; Jian Guo Dong; Nina Berova

doi:10.1016/0040-4039(95)00523-F

Enzymatic resolution of a key stereochemical intermediate for the synthesis of (-)-taxol

Carl R. Johnson, Yanping Xu, K. C. Nicolaou, Zhen Yang, Rodney K. Guy, Jian Guo Dong, Nina Berova

Research output: Contribution to journal › Article › peer-review

33 Scopus citations

Abstract

The taxol intermediate, racemic 3, was subjected to two consecutive kinetic resolutions with recombinant Candida antarctica lipase B in isopropenyl acetate/hexane. The absolute stereochemistry of the resulting acetate (+)-5 of > 99% enantiopurity, was assigned based on NMR and CD methods.

Original language	English
Pages (from-to)	3291-3294
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	19
DOIs	https://doi.org/10.1016/0040-4039(95)00523-F
State	Published - May 8 1995

Bibliographical note

Funding Information:
secondw ill be locatedn ear1 95n m,a ndt hereforeb, ed ifficultt o measured),e noteas positivec hiralityb etween thep -bromobenzoaanted t he2 -enea ndc onfirmtsh eS -configuratioant t hec yclicc arbinocl enter. Basedo n thea boveli neso f evidencew, e concludeth att hed iol enantiomeprr eferrebdy the Candida antarcticali paseB is of thec orrecat bsolutceo nfiguratiofno rt hes ynthesiosf natura(l-)-taxol. AcknowledgmentT. he work at WayneS tateU niversityw as madep ossibleb y a grant (CHE-9223011)f romt heN ationaSl cienceF oundationf;in anciasl upporfto rThe ScrippsR esearcIhn stituteg roupw as providedb y The NationaIln stituteso f Health,U SA anda fellowshipfr omthe Office of NavalR esearch(t o R.K.G.). We thankD r. S. E. Godtfredseonf Novo NordiskA /S for theS P-435b iocatalyst. References and Notes (1) For a recenrte views eeR owinskyE, . K.; OnettoN, .; CanettaR, . M.; Arbuck,S . G. SeminO. ncol. 1992,1 9, 646. (2) Wani, M. C.; Taylor,H . L.; Wall, M. E.; CoggonP, .; McPhail,A . T. J. Am. Chem.Soc.1971,93, 2325. (3) For reviewss ee( a) NicolaouK, . C.; Dai, W.-M.; Guy, R. K. Angew.C hem.I nt. Ed. Engl. 1992,3 3, 15;( b) GutnardD, .; Gu~ritte-VoegeleiFn.,; Potier,P . Acc. Chem.R es. 1993,2 6, 160;( c) Tetrahedron Symposia-in-prinTte, trahedro1n9 92,4 8 (34). (4) Holton,R . A.; Kim, H.-B.; SomozaC, .; Liang,F ..; Biediger,R . J.; BoatmanP,. D.; Shindo,M .; Smith, C. C.; Kim, S.; NadizadehH, .; Suzuki,Y .; Tat, C.; Vu P.; Tang,S .;, ZhangP, .; Murthi,K . K.; Gentile, L. N.; Liu, J. H. J. Am. Chem.S oc. 1994,1 16, 1599. (5) (a) NicolaouK, . C.; Yang,Z .; Liu, J. J.; Ueno,H .; NantermetP,. G.; Guy, R. K.; ClaiborneC, . F.; RenaudJ,. ; CouladouroEs,. A.; PaulvannanK,. ; SorensenE, . J. Nature 1994,3 67, 630. (b) Nicolaou, K.C.; Ueno,H .; Liu, J.-J.; NantermePt,. G.; Yang,Z .; RenaudJ,. ; PaulvannanK,. ; ChadhaR, . J. Am. Chem.S oc. 1995,1 17,6 53a ndp recedinpga pers. (6) Bis, S. J., Whitaker,D . T.; JohnsonC, . R. TetrahedronA:s ymmetr1y9 93,4 , 875;J ohnsonC, . R.; SakaguchiH, . Synlett1 992,8 13. (7) For a recenrte viewo fu seo f lipasesf ort ransesterificatioinn so rganicm edias eeW ong,C .-H.;Whitesides, G. M. Enzymeisn SynthetiOc rganicC hemistryE, lsevierS cienceO: xford.E ngland1, 984;p . 72. (8) Ihara,M .; Suzuki,M .; FukumotoK, .; Kabuto,C ., J. Am. Chem.S oc.19901,1 2, 1164. (9) EstermannH,. ; Prasad,K .; Shapiro,M . J.; Repic,O .; HardtmanG, . E.; Bolsterli,J . J.; WlakinshawM, . D.; TetrahedroLne tt. 1990,3 1, 445. (10) FerraboschPi,. ; BrembillaD, .; Grisenti,P .; SantanielloE, . J. Org. Chem.1 991,5 6, 5478. (11) Randrianasolo-RakotozLa.f Ry.,; AzeradR, .; DumasF, .; Potin,D .; d'AngeloJ,. Tetrahedron: Asymmetr1y9 93,4 , 761. (12) Wang,Y .-F.; LalondeJ,. J.; MomonganM, .; BergbreiterD, . E.; Wong,C .-H. J. Am. Chem.S oc. 1988,1 10, 7200. (13) For othere xampleosf sequentiakli neticr esolutionsse e: Lin, G.; Chen.S .-J.; Sun,H .-L. J. Chinese. Chem.S oc. 1994,4 1, 459; Chen,C .-S.; Liu, Y.-C. J. Org. Chem.1 991,5 6, 1966; Fowler,P . W.; MacfarlaneE,. L. A.; RobertsS, . M. J. Chem.S oc., Chem.C ommun1. 991,4 53;B rieva,R .; RebolledoF,. ; Gotor,V . J. Chem.S oc., Chem.C ommun.1 991,1 386; MacfarlandE,. L. A.; Roberts, S. M.; Turner,N . J., J. Chem.S oc., Chem.C ommun1. 990,5 69;T heil, F.; Kunath,A .; Schick,H . TetrahedroLne tt. 1992,3 3, 3457;W ang,Y .-F.; Chen,C .-S.;G irdaukasG, .; Sih, C. J. J. Am. Chem. Soc. 1984,1 06, 3695. (14) DokuzoviZ,. ; RobertsN, . K.; SawyerJ,. F.; Whelan,J.; BosnichB, . J. Am. Chem.Soc.1986,108, 2034. (15) Gut, Z.-W.; Wu, S.-H.; Chen,C .-S.; GirdaukasG, .; Sih, C. J. J. Am. Chem.S oc. 1990,1 12, 4943. (16) Trost,B . M.; Belletire,J . L.; GodleskiS, .; McDougalP, . G.; Balkovec,J . M.; Baldwin,J . J.; Christy, M. E.; PonticelloG, . S.; Varga,S . L., SpringerJ,. P. J. Org. Chem.1 986,5 1, 2370. (17) Bagli, J. F.; Morand,P . F.; GaudryR, . J. J. Org. Chem..196238, , 1207. (18) SnatzkeG, .; SnatzkeF. In FundamentAasl pectas ndR ecenDt evelopmenints O pticalR otatoryD ispersion and CircularD ichroismC, iardelli,F .; SalavadoriP, . Eds.;H eydenL: ondon,1 973;p p. 109-121. (19) NakanishiK, .; BerovaN, . In CircularD ichroismP rinciplesa ndA pplicationsN, akanishiK, .; BerovaN, .; Woody,R . W., Eds.: VCH: New York, 1994;C hapte1r 3.

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4039(95)00523-F

Cite this

@article{9c38cafb43724aed97ec91a1318bb918,

title = "Enzymatic resolution of a key stereochemical intermediate for the synthesis of (-)-taxol",

abstract = "The taxol intermediate, racemic 3, was subjected to two consecutive kinetic resolutions with recombinant Candida antarctica lipase B in isopropenyl acetate/hexane. The absolute stereochemistry of the resulting acetate (+)-5 of > 99% enantiopurity, was assigned based on NMR and CD methods.",

author = "Johnson, {Carl R.} and Yanping Xu and Nicolaou, {K. C.} and Zhen Yang and Guy, {Rodney K.} and Dong, {Jian Guo} and Nina Berova",

note = "Funding Information: secondw ill be locatedn ear1 95n m,a ndt hereforeb, ed ifficultt o measured),e noteas positivec hiralityb etween thep -bromobenzoaanted t he2 -enea ndc onfirmtsh eS -configuratioant t hec yclicc arbinocl enter. Basedo n thea boveli neso f evidencew, e concludeth att hed iol enantiomeprr eferrebdy the Candida antarcticali paseB is of thec orrecat bsolutceo nfiguratiofno rt hes ynthesiosf natura(l-)-taxol. AcknowledgmentT. he work at WayneS tateU niversityw as madep ossibleb y a grant (CHE-9223011)f romt heN ationaSl cienceF oundationf;in anciasl upporfto rThe ScrippsR esearcIhn stituteg roupw as providedb y The NationaIln stituteso f Health,U SA anda fellowshipfr omthe Office of NavalR esearch(t o R.K.G.). We thankD r. S. E. Godtfredseonf Novo NordiskA /S for theS P-435b iocatalyst. References and Notes (1) For a recenrte views eeR owinskyE, . K.; OnettoN, .; CanettaR, . M.; Arbuck,S . G. SeminO. ncol. 1992,1 9, 646. (2) Wani, M. C.; Taylor,H . L.; Wall, M. E.; CoggonP, .; McPhail,A . T. J. Am. Chem.Soc.1971,93, 2325. (3) For reviewss ee( a) NicolaouK, . C.; Dai, W.-M.; Guy, R. K. Angew.C hem.I nt. Ed. Engl. 1992,3 3, 15;( b) GutnardD, .; Gu~ritte-VoegeleiFn.,; Potier,P . Acc. Chem.R es. 1993,2 6, 160;( c) Tetrahedron Symposia-in-prinTte, trahedro1n9 92,4 8 (34). (4) Holton,R . A.; Kim, H.-B.; SomozaC, .; Liang,F ..; Biediger,R . J.; BoatmanP,. D.; Shindo,M .; Smith, C. C.; Kim, S.; NadizadehH, .; Suzuki,Y .; Tat, C.; Vu P.; Tang,S .;, ZhangP, .; Murthi,K . K.; Gentile, L. N.; Liu, J. H. J. Am. Chem.S oc. 1994,1 16, 1599. (5) (a) NicolaouK, . C.; Yang,Z .; Liu, J. J.; Ueno,H .; NantermetP,. G.; Guy, R. K.; ClaiborneC, . F.; RenaudJ,. ; CouladouroEs,. A.; PaulvannanK,. ; SorensenE, . J. Nature 1994,3 67, 630. (b) Nicolaou, K.C.; Ueno,H .; Liu, J.-J.; NantermePt,. G.; Yang,Z .; RenaudJ,. ; PaulvannanK,. ; ChadhaR, . J. Am. Chem.S oc. 1995,1 17,6 53a ndp recedinpga pers. (6) Bis, S. J., Whitaker,D . T.; JohnsonC, . R. TetrahedronA:s ymmetr1y9 93,4 , 875;J ohnsonC, . R.; SakaguchiH, . Synlett1 992,8 13. (7) For a recenrte viewo fu seo f lipasesf ort ransesterificatioinn so rganicm edias eeW ong,C .-H.;Whitesides, G. M. Enzymeisn SynthetiOc rganicC hemistryE, lsevierS cienceO: xford.E ngland1, 984;p . 72. (8) Ihara,M .; Suzuki,M .; FukumotoK, .; Kabuto,C ., J. Am. Chem.S oc.19901,1 2, 1164. (9) EstermannH,. ; Prasad,K .; Shapiro,M . J.; Repic,O .; HardtmanG, . E.; Bolsterli,J . J.; WlakinshawM, . D.; TetrahedroLne tt. 1990,3 1, 445. (10) FerraboschPi,. ; BrembillaD, .; Grisenti,P .; SantanielloE, . J. Org. Chem.1 991,5 6, 5478. (11) Randrianasolo-RakotozLa.f Ry.,; AzeradR, .; DumasF, .; Potin,D .; d'AngeloJ,. Tetrahedron: Asymmetr1y9 93,4 , 761. (12) Wang,Y .-F.; LalondeJ,. J.; MomonganM, .; BergbreiterD, . E.; Wong,C .-H. J. Am. Chem.S oc. 1988,1 10, 7200. (13) For othere xampleosf sequentiakli neticr esolutionsse e: Lin, G.; Chen.S .-J.; Sun,H .-L. J. Chinese. Chem.S oc. 1994,4 1, 459; Chen,C .-S.; Liu, Y.-C. J. Org. Chem.1 991,5 6, 1966; Fowler,P . W.; MacfarlaneE,. L. A.; RobertsS, . M. J. Chem.S oc., Chem.C ommun1. 991,4 53;B rieva,R .; RebolledoF,. ; Gotor,V . J. Chem.S oc., Chem.C ommun.1 991,1 386; MacfarlandE,. L. A.; Roberts, S. M.; Turner,N . J., J. Chem.S oc., Chem.C ommun1. 990,5 69;T heil, F.; Kunath,A .; Schick,H . TetrahedroLne tt. 1992,3 3, 3457;W ang,Y .-F.; Chen,C .-S.;G irdaukasG, .; Sih, C. J. J. Am. Chem. Soc. 1984,1 06, 3695. (14) DokuzoviZ,. ; RobertsN, . K.; SawyerJ,. F.; Whelan,J.; BosnichB, . J. Am. Chem.Soc.1986,108, 2034. (15) Gut, Z.-W.; Wu, S.-H.; Chen,C .-S.; GirdaukasG, .; Sih, C. J. J. Am. Chem.S oc. 1990,1 12, 4943. (16) Trost,B . M.; Belletire,J . L.; GodleskiS, .; McDougalP, . G.; Balkovec,J . M.; Baldwin,J . J.; Christy, M. E.; PonticelloG, . S.; Varga,S . L., SpringerJ,. P. J. Org. Chem.1 986,5 1, 2370. (17) Bagli, J. F.; Morand,P . F.; GaudryR, . J. J. Org. Chem..196238, , 1207. (18) SnatzkeG, .; SnatzkeF. In FundamentAasl pectas ndR ecenDt evelopmenints O pticalR otatoryD ispersion and CircularD ichroismC, iardelli,F .; SalavadoriP, . Eds.;H eydenL: ondon,1 973;p p. 109-121. (19) NakanishiK, .; BerovaN, . In CircularD ichroismP rinciplesa ndA pplicationsN, akanishiK, .; BerovaN, .; Woody,R . W., Eds.: VCH: New York, 1994;C hapte1r 3.",

year = "1995",

month = may,

day = "8",

doi = "10.1016/0040-4039(95)00523-F",

language = "English",

volume = "36",

pages = "3291--3294",

number = "19",

}

TY - JOUR

T1 - Enzymatic resolution of a key stereochemical intermediate for the synthesis of (-)-taxol

AU - Johnson, Carl R.

AU - Xu, Yanping

AU - Nicolaou, K. C.

AU - Yang, Zhen

AU - Guy, Rodney K.

AU - Dong, Jian Guo

AU - Berova, Nina

N1 - Funding Information: secondw ill be locatedn ear1 95n m,a ndt hereforeb, ed ifficultt o measured),e noteas positivec hiralityb etween thep -bromobenzoaanted t he2 -enea ndc onfirmtsh eS -configuratioant t hec yclicc arbinocl enter. Basedo n thea boveli neso f evidencew, e concludeth att hed iol enantiomeprr eferrebdy the Candida antarcticali paseB is of thec orrecat bsolutceo nfiguratiofno rt hes ynthesiosf natura(l-)-taxol. AcknowledgmentT. he work at WayneS tateU niversityw as madep ossibleb y a grant (CHE-9223011)f romt heN ationaSl cienceF oundationf;in anciasl upporfto rThe ScrippsR esearcIhn stituteg roupw as providedb y The NationaIln stituteso f Health,U SA anda fellowshipfr omthe Office of NavalR esearch(t o R.K.G.). We thankD r. S. E. Godtfredseonf Novo NordiskA /S for theS P-435b iocatalyst. References and Notes (1) For a recenrte views eeR owinskyE, . K.; OnettoN, .; CanettaR, . M.; Arbuck,S . G. SeminO. ncol. 1992,1 9, 646. (2) Wani, M. C.; Taylor,H . L.; Wall, M. E.; CoggonP, .; McPhail,A . T. J. Am. Chem.Soc.1971,93, 2325. (3) For reviewss ee( a) NicolaouK, . C.; Dai, W.-M.; Guy, R. K. Angew.C hem.I nt. Ed. Engl. 1992,3 3, 15;( b) GutnardD, .; Gu~ritte-VoegeleiFn.,; Potier,P . Acc. Chem.R es. 1993,2 6, 160;( c) Tetrahedron Symposia-in-prinTte, trahedro1n9 92,4 8 (34). (4) Holton,R . A.; Kim, H.-B.; SomozaC, .; Liang,F ..; Biediger,R . J.; BoatmanP,. D.; Shindo,M .; Smith, C. C.; Kim, S.; NadizadehH, .; Suzuki,Y .; Tat, C.; Vu P.; Tang,S .;, ZhangP, .; Murthi,K . K.; Gentile, L. N.; Liu, J. H. J. Am. Chem.S oc. 1994,1 16, 1599. (5) (a) NicolaouK, . C.; Yang,Z .; Liu, J. J.; Ueno,H .; NantermetP,. G.; Guy, R. K.; ClaiborneC, . F.; RenaudJ,. ; CouladouroEs,. A.; PaulvannanK,. ; SorensenE, . J. Nature 1994,3 67, 630. (b) Nicolaou, K.C.; Ueno,H .; Liu, J.-J.; NantermePt,. G.; Yang,Z .; RenaudJ,. ; PaulvannanK,. ; ChadhaR, . J. Am. Chem.S oc. 1995,1 17,6 53a ndp recedinpga pers. (6) Bis, S. J., Whitaker,D . T.; JohnsonC, . R. TetrahedronA:s ymmetr1y9 93,4 , 875;J ohnsonC, . R.; SakaguchiH, . Synlett1 992,8 13. (7) For a recenrte viewo fu seo f lipasesf ort ransesterificatioinn so rganicm edias eeW ong,C .-H.;Whitesides, G. M. Enzymeisn SynthetiOc rganicC hemistryE, lsevierS cienceO: xford.E ngland1, 984;p . 72. (8) Ihara,M .; Suzuki,M .; FukumotoK, .; Kabuto,C ., J. Am. Chem.S oc.19901,1 2, 1164. (9) EstermannH,. ; Prasad,K .; Shapiro,M . J.; Repic,O .; HardtmanG, . E.; Bolsterli,J . J.; WlakinshawM, . D.; TetrahedroLne tt. 1990,3 1, 445. (10) FerraboschPi,. ; BrembillaD, .; Grisenti,P .; SantanielloE, . J. Org. Chem.1 991,5 6, 5478. (11) Randrianasolo-RakotozLa.f Ry.,; AzeradR, .; DumasF, .; Potin,D .; d'AngeloJ,. Tetrahedron: Asymmetr1y9 93,4 , 761. (12) Wang,Y .-F.; LalondeJ,. J.; MomonganM, .; BergbreiterD, . E.; Wong,C .-H. J. Am. Chem.S oc. 1988,1 10, 7200. (13) For othere xampleosf sequentiakli neticr esolutionsse e: Lin, G.; Chen.S .-J.; Sun,H .-L. J. Chinese. Chem.S oc. 1994,4 1, 459; Chen,C .-S.; Liu, Y.-C. J. Org. Chem.1 991,5 6, 1966; Fowler,P . W.; MacfarlaneE,. L. A.; RobertsS, . M. J. Chem.S oc., Chem.C ommun1. 991,4 53;B rieva,R .; RebolledoF,. ; Gotor,V . J. Chem.S oc., Chem.C ommun.1 991,1 386; MacfarlandE,. L. A.; Roberts, S. M.; Turner,N . J., J. Chem.S oc., Chem.C ommun1. 990,5 69;T heil, F.; Kunath,A .; Schick,H . TetrahedroLne tt. 1992,3 3, 3457;W ang,Y .-F.; Chen,C .-S.;G irdaukasG, .; Sih, C. J. J. Am. Chem. Soc. 1984,1 06, 3695. (14) DokuzoviZ,. ; RobertsN, . K.; SawyerJ,. F.; Whelan,J.; BosnichB, . J. Am. Chem.Soc.1986,108, 2034. (15) Gut, Z.-W.; Wu, S.-H.; Chen,C .-S.; GirdaukasG, .; Sih, C. J. J. Am. Chem.S oc. 1990,1 12, 4943. (16) Trost,B . M.; Belletire,J . L.; GodleskiS, .; McDougalP, . G.; Balkovec,J . M.; Baldwin,J . J.; Christy, M. E.; PonticelloG, . S.; Varga,S . L., SpringerJ,. P. J. Org. Chem.1 986,5 1, 2370. (17) Bagli, J. F.; Morand,P . F.; GaudryR, . J. J. Org. Chem..196238, , 1207. (18) SnatzkeG, .; SnatzkeF. In FundamentAasl pectas ndR ecenDt evelopmenints O pticalR otatoryD ispersion and CircularD ichroismC, iardelli,F .; SalavadoriP, . Eds.;H eydenL: ondon,1 973;p p. 109-121. (19) NakanishiK, .; BerovaN, . In CircularD ichroismP rinciplesa ndA pplicationsN, akanishiK, .; BerovaN, .; Woody,R . W., Eds.: VCH: New York, 1994;C hapte1r 3.

PY - 1995/5/8

Y1 - 1995/5/8

N2 - The taxol intermediate, racemic 3, was subjected to two consecutive kinetic resolutions with recombinant Candida antarctica lipase B in isopropenyl acetate/hexane. The absolute stereochemistry of the resulting acetate (+)-5 of > 99% enantiopurity, was assigned based on NMR and CD methods.

AB - The taxol intermediate, racemic 3, was subjected to two consecutive kinetic resolutions with recombinant Candida antarctica lipase B in isopropenyl acetate/hexane. The absolute stereochemistry of the resulting acetate (+)-5 of > 99% enantiopurity, was assigned based on NMR and CD methods.

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UR - http://www.scopus.com/inward/citedby.url?scp=0028922396&partnerID=8YFLogxK

U2 - 10.1016/0040-4039(95)00523-F

DO - 10.1016/0040-4039(95)00523-F

M3 - Article

AN - SCOPUS:0028922396

SN - 0040-4039

VL - 36

SP - 3291

EP - 3294

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 19

ER -

Enzymatic resolution of a key stereochemical intermediate for the synthesis of (-)-taxol

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