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Volumn 345, Issue 6-7, 2003, Pages 766-774

Enantiomerically Pure Octahydronaphthalenone and Octahydroindenone: Elaboration of the Substrate Overcame the Specificity of Yeast-Mediated Reduction

(3) Fuhshuku, Ken Ichi a Tomita, Mina a Sugai, Takeshi a

a KEIO UNIVERSITY (Japan)

Author keywords

Chiral building block; Desymmetrization; Kinetic resolution; Prochiral substrate; Reduction; Terpenoid; Whole cell biocatalyst; Yeast

Indexed keywords

3 ETHYL 3 HYDROXY 6 METHYL 2 OXABICYCLO[4.4.0]DECAN 7 ONE; 3 HYDROXY 3,6 DIMETHYL 2 OXABICYCLO[4.3.0]NONAN 7 ONE; ACETAL DERIVATIVE; CARBONYL DERIVATIVE; FUNCTIONAL GROUP; INDENE DERIVATIVE; KETONE DERIVATIVE; NAPHTHALENE; OCTAHYDROINDENONE; OCTAHYDRONAPHTHALENONE; OXIDOREDUCTASE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME SPECIFICITY; EXTRACTION; FUNGAL CELL; FUNGAL STRAIN; OXIDATION REDUCTION REACTION; REDUCTION; STEREOCHEMISTRY; SUBSTITUTION REACTION; YEAST;

EID: 0043134445 PISSN: 16154150 EISSN: None Source Type: Journal
DOI: 10.1002/adsc.200303004 Document Type: Article

Times cited : (27)

References (39)

1
- 0033963525
- K. Fuhshuku, N. Funa, T. Akeboshi, H. Ohta, H. Hosomi, S. Ohba, T. Sugai, J. Org. Chem. 2000, 65, 129-135.
- (2000) J. Org. Chem. , vol.65 , pp. 129-135
- Fuhshuku, K.¹ Funa, N.² Akeboshi, T.³ Ohta, H.⁴ Hosomi, H.⁵ Ohba, S.⁶ Sugai, T.⁷

2
- 0000096617
- For recent examples from (R)-1, see: a) A. B. Smith, III, J. Kingery-Wood, T. L. Leenay, E. G. Nolen, T. Sunazuka, J. Am. Chem. Soc. 1992, 114, 1438-1449; b) L. A. Paquette, H.-L. Wang, J. Org. Chem. 1996, 61, 5352-5357; c) L. A. Paquette, D. Backhaus, R. Braun, T. L. Underiner, K. Fuchs, J. Am. Chem. Soc. 1997, 119, 9662-9671; d) A. Yajima, K. Mori, Eur. J. Org. Chem. 2000, 4079-4091; e) T. Ling, C. Chowdhury, B. A. Kramer, B. G. Vong, M. A. Palladino, E. A. Theodrakis, J. Org. Chem. 2001, 66, 8843-8853.
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 1438-1449
- Smith III, A.B.¹ Kingery-Wood, J.² Leenay, T.L.³ Nolen, E.G.⁴ Sunazuka, T.⁵

3
- 0029743531
- For recent examples from (R)-1, see: a) A. B. Smith, III, J. Kingery-Wood, T. L. Leenay, E. G. Nolen, T. Sunazuka, J. Am. Chem. Soc. 1992, 114, 1438-1449; b) L. A. Paquette, H.-L. Wang, J. Org. Chem. 1996, 61, 5352-5357; c) L. A. Paquette, D. Backhaus, R. Braun, T. L. Underiner, K. Fuchs, J. Am. Chem. Soc. 1997, 119, 9662-9671; d) A. Yajima, K. Mori, Eur. J. Org. Chem. 2000, 4079-4091; e) T. Ling, C. Chowdhury, B. A. Kramer, B. G. Vong, M. A. Palladino, E. A. Theodrakis, J. Org. Chem. 2001, 66, 8843-8853.
- (1996) J. Org. Chem. , vol.61 , pp. 5352-5357
- Paquette, L.A.¹ Wang, H.-L.²

4
- 0030691768
- For recent examples from (R)-1, see: a) A. B. Smith, III, J. Kingery-Wood, T. L. Leenay, E. G. Nolen, T. Sunazuka, J. Am. Chem. Soc. 1992, 114, 1438-1449; b) L. A. Paquette, H.-L. Wang, J. Org. Chem. 1996, 61, 5352-5357; c) L. A. Paquette, D. Backhaus, R. Braun, T. L. Underiner, K. Fuchs, J. Am. Chem. Soc. 1997, 119, 9662-9671; d) A. Yajima, K. Mori, Eur. J. Org. Chem. 2000, 4079-4091; e) T. Ling, C. Chowdhury, B. A. Kramer, B. G. Vong, M. A. Palladino, E. A. Theodrakis, J. Org. Chem. 2001, 66, 8843-8853.
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 9662-9671
- Paquette, L.A.¹ Backhaus, D.² Braun, R.³ Underiner, T.L.⁴ Fuchs, K.⁵

5
- 0002509684
- For recent examples from (R)-1, see: a) A. B. Smith, III, J. Kingery-Wood, T. L. Leenay, E. G. Nolen, T. Sunazuka, J. Am. Chem. Soc. 1992, 114, 1438-1449; b) L. A. Paquette, H.-L. Wang, J. Org. Chem. 1996, 61, 5352-5357; c) L. A. Paquette, D. Backhaus, R. Braun, T. L. Underiner, K. Fuchs, J. Am. Chem. Soc. 1997, 119, 9662-9671; d) A. Yajima, K. Mori, Eur. J. Org. Chem. 2000, 4079-4091; e) T. Ling, C. Chowdhury, B. A. Kramer, B. G. Vong, M. A. Palladino, E. A. Theodrakis, J. Org. Chem. 2001, 66, 8843-8853.
- (2000) Eur. J. Org. Chem. , pp. 4079-4091
- Yajima, A.¹ Mori, K.²

6
- 0035966238
- For recent examples from (R)-1, see: a) A. B. Smith, III, J. Kingery-Wood, T. L. Leenay, E. G. Nolen, T. Sunazuka, J. Am. Chem. Soc. 1992, 114, 1438-1449; b) L. A. Paquette, H.-L. Wang, J. Org. Chem. 1996, 61, 5352-5357; c) L. A. Paquette, D. Backhaus, R. Braun, T. L. Underiner, K. Fuchs, J. Am. Chem. Soc. 1997, 119, 9662-9671; d) A. Yajima, K. Mori, Eur. J. Org. Chem. 2000, 4079-4091; e) T. Ling, C. Chowdhury, B. A. Kramer, B. G. Vong, M. A. Palladino, E. A. Theodrakis, J. Org. Chem. 2001, 66, 8843-8853.
- (2001) J. Org. Chem. , vol.66 , pp. 8843-8853
- Ling, T.¹ Chowdhury, C.² Kramer, B.A.³ Vong, B.G.⁴ Palladino, M.A.⁵ Theodrakis, E.A.⁶

7
- 11044223276
- For recent examples from (S)-1, see: a) S. J. Danishefsky, J. J. Masters, W. B. Young, J. T. Link, L. B. Snyder, T. V. Magee, D. K. Jung, R. C. A. Isaacs, W. G. Bornmann, C. A. Alaimo, C. A. Coburn, M. J. Di Grandi, J. Am. Chem. Soc. 1996, 118, 2843-2859; b) J. An, D. F. Wiemer, J. Org. Chem. 1996, 61, 8775-8779; c) A. Pemp, K. Seifert, Tetrahedron Lett. 1997, 38, 2081-2084; d) W. S. Cheung, H. N. C. Wong, Tetrahedron 1999, 55, 11001-11016; e) K. Fuhshuku, T. Sugai, Biosci. Biotechnol. Biochem. 2002, 66, 2267-2272.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 2843-2859
- Danishefsky, S.J.¹ Masters, J.J.² Young, W.B.³ Link, J.T.⁴ Snyder, L.B.⁵ Magee, T.V.⁶ Jung, D.K.⁷ Isaacs, R.C.A.⁸ Bornmann, W.G.⁹ Alaimo, C.A.¹⁰ Coburn, C.A.¹¹ Di Grandi, M.J.¹²

8
- 0030443456
- For recent examples from (S)-1, see: a) S. J. Danishefsky, J. J. Masters, W. B. Young, J. T. Link, L. B. Snyder, T. V. Magee, D. K. Jung, R. C. A. Isaacs, W. G. Bornmann, C. A. Alaimo, C. A. Coburn, M. J. Di Grandi, J. Am. Chem. Soc. 1996, 118, 2843-2859; b) J. An, D. F. Wiemer, J. Org. Chem. 1996, 61, 8775-8779; c) A. Pemp, K. Seifert, Tetrahedron Lett. 1997, 38, 2081-2084; d) W. S. Cheung, H. N. C. Wong, Tetrahedron 1999, 55, 11001-11016; e) K. Fuhshuku, T. Sugai, Biosci. Biotechnol. Biochem. 2002, 66, 2267-2272.
- (1996) J. Org. Chem. , vol.61 , pp. 8775-8779
- An, J.¹ Wiemer, D.F.²

9
- 0031585096
- For recent examples from (S)-1, see: a) S. J. Danishefsky, J. J. Masters, W. B. Young, J. T. Link, L. B. Snyder, T. V. Magee, D. K. Jung, R. C. A. Isaacs, W. G. Bornmann, C. A. Alaimo, C. A. Coburn, M. J. Di Grandi, J. Am. Chem. Soc. 1996, 118, 2843-2859; b) J. An, D. F. Wiemer, J. Org. Chem. 1996, 61, 8775-8779; c) A. Pemp, K. Seifert, Tetrahedron Lett. 1997, 38, 2081-2084; d) W. S. Cheung, H. N. C. Wong, Tetrahedron 1999, 55, 11001-11016; e) K. Fuhshuku, T. Sugai, Biosci. Biotechnol. Biochem. 2002, 66, 2267-2272.
- (1997) Tetrahedron Lett. , vol.38 , pp. 2081-2084
- Pemp, A.¹ Seifert, K.²

10
- 0033520254
- For recent examples from (S)-1, see: a) S. J. Danishefsky, J. J. Masters, W. B. Young, J. T. Link, L. B. Snyder, T. V. Magee, D. K. Jung, R. C. A. Isaacs, W. G. Bornmann, C. A. Alaimo, C. A. Coburn, M. J. Di Grandi, J. Am. Chem. Soc. 1996, 118, 2843-2859; b) J. An, D. F. Wiemer, J. Org. Chem. 1996, 61, 8775-8779; c) A. Pemp, K. Seifert, Tetrahedron Lett. 1997, 38, 2081-2084; d) W. S. Cheung, H. N. C. Wong, Tetrahedron 1999, 55, 11001-11016; e) K. Fuhshuku, T. Sugai, Biosci. Biotechnol. Biochem. 2002, 66, 2267-2272.
- (1999) Tetrahedron , vol.55 , pp. 11001-11016
- Cheung, W.S.¹ Wong, H.N.C.²

11
- 0242634695
- For recent examples from (S)-1, see: a) S. J. Danishefsky, J. J. Masters, W. B. Young, J. T. Link, L. B. Snyder, T. V. Magee, D. K. Jung, R. C. A. Isaacs, W. G. Bornmann, C. A. Alaimo, C. A. Coburn, M. J. Di Grandi, J. Am. Chem. Soc. 1996, 118, 2843-2859; b) J. An, D. F. Wiemer, J. Org. Chem. 1996, 61, 8775-8779; c) A. Pemp, K. Seifert, Tetrahedron Lett. 1997, 38, 2081-2084; d) W. S. Cheung, H. N. C. Wong, Tetrahedron 1999, 55, 11001-11016; e) K. Fuhshuku, T. Sugai, Biosci. Biotechnol. Biochem. 2002, 66, 2267-2272.
- (2002) Biosci. Biotechnol. Biochem. , vol.66 , pp. 2267-2272
- Fuhshuku, K.¹ Sugai, T.²

12
- 0011189290
- K. Fuhshuku, S. Oda, T. Sugai, Recent Res. Devel. Org. Chem. 2002, 6, 57-74.
- (2002) Recent Res. Devel. Org. Chem. , vol.6 , pp. 57-74
- Fuhshuku, K.¹ Oda, S.² Sugai, T.³

13
- 0007850440
- a) V. Prelog, W. Acklin, Helv. Chim. Acta 1956, 39, 748-757;
- (1956) Helv. Chim. Acta , vol.39 , pp. 748-757
- Prelog, V.¹ Acklin, W.²

14
- 84984083657
- b) W. Acklin, V. Prelog, A. P. Prieto, Helv. Chim. Acta 1958, 41, 1416-1424;
- (1958) Helv. Chim. Acta , vol.41 , pp. 1416-1424
- Acklin, W.¹ Prelog, V.² Prieto, A.P.³

15
- 84984086930
- c) W. Acklin, D. Dütting, V. Prelog. Helv. Chim. Acta 1958, 41, 1424-1427;
- (1958) Helv. Chim. Acta , vol.41 , pp. 1424-1427
- Acklin, W.¹ Dütting, D.² Prelog, V.³

16
- 84984084159
- d) W. Acklin, V. Prelog, D. Zäch, Helv. Chim. Acta 1958, 41, 1428-1437.
- (1958) Helv. Chim. Acta , vol.41 , pp. 1428-1437
- Acklin, W.¹ Prelog, V.² Zäch, D.³

17
- 85004596168
- a) S. Inayama, N. Shimizu, T. Ohkura, H. Akita, T. Oishi, Y. Iitaka, Chem. Pharm. Bull. 1986, 33, 2660-2663;
- (1986) Chem. Pharm. Bull. , vol.33 , pp. 2660-2663
- Inayama, S.¹ Shimizu, N.² Ohkura, T.³ Akita, H.⁴ Oishi, T.⁵ Iitaka, Y.⁶

18
- 85004246502
- b) S. Inayama, N. Shimizu, T. Ohkura, H. Akita, T. Oishi, Y. Iitaka, Chem. Pharm. Bull. 1987, 35, 429-432.
- (1987) Chem. Pharm. Bull. , vol.35 , pp. 429-432
- Inayama, S.¹ Shimizu, N.² Ohkura, T.³ Akita, H.⁴ Oishi, T.⁵ Iitaka, Y.⁶

19
- 0034712278
- H. Hioki, T. Hashimoto, M. Kodama, Tetrahedron Asymmetry 2000, 11, 829-834.
- (2000) Tetrahedron Asymmetry , vol.11 , pp. 829-834
- Hioki, H.¹ Hashimoto, T.² Kodama, M.³

20
- 20644469267
- C.-S. Chen, Y. Fujimoto, G. Girdaukas, C. J. Sih, J. Am. Chem. Soc. 1982, 104, 7294-7299.
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 7294-7299
- Chen, C.-S.¹ Fujimoto, Y.² Girdaukas, G.³ Sih, C.J.⁴

21
- 84920564546
- a) S. Servi, Synthesis 1990, 1-25;
- (1990) Synthesis , pp. 1-25
- Servi, S.¹

22
- 12044253833
- b) R. Csuk, B. I. Glänzer, Chem. Rev. 1991, 91, 49-97;
- (1991) Chem. Rev. , vol.91 , pp. 49-97
- Csuk, R.¹ Glänzer, B.I.²

23
- 0032807862
- c) T. Sugai, Curr. Org. Chem. 1999, 3, 373-406.
- (1999) Curr. Org. Chem. , vol.3 , pp. 373-406
- Sugai, T.¹

24
- 0026648225
- a) G. Dauphin, J.-G. Gourcy, H. Veschambre, Tetrahedron Asymmetry 1992, 3, 595-598;
- (1992) Tetrahedron Asymmetry , vol.3 , pp. 595-598
- Dauphin, G.¹ Gourcy, J.-G.² Veschambre, H.³

25
- 0035956409
- b) Y. Kawai, M. Hayashi, N. Tokitoh, Tetrahedron Asymmetry 2001, 12, 3007-3013.
- (2001) Tetrahedron Asymmetry , vol.12 , pp. 3007-3013
- Kawai, Y.¹ Hayashi, M.² Tokitoh, N.³

26
- 0242719017
- a) W. Zhou, D. Huang, Z. Wang, Kexue Tongbao 1980, 25, 741-742;
- (1980) Kexue Tongbao , vol.25 , pp. 741-742
- Zhou, W.¹ Huang, D.² Wang, Z.³

27
- 0242719018
- b) W. Zhou, D. Huang, Q. Dong, Z. Zhuang, Z. Wang, Chem. Nat. Prod., Proc. Sino-Am. Symp. 1980, 299-301;
- (1980) Chem. Nat. Prod., Proc. Sino-Am. Symp. , pp. 299-301
- Zhou, W.¹ Huang, D.² Dong, Q.³ Zhuang, Z.⁴ Wang, Z.⁵

28
- 0005135169
- c) W. Zhou, D. Huang, Q. Dong, Z. Wang, Acta Chimica Sinica (Huaxue Xuebao) 1982, 40, 648-656;
- (1982) Acta Chimica Sinica (Huaxue Xuebao) , vol.40 , pp. 648-656
- Zhou, W.¹ Huang, D.² Dong, Q.³ Wang, Z.⁴

29
- 0242549897
- d) W. Zhou, Z. Zhuang, Z. Wang, Acta Chimica Sinica (Huaxue Xuebao) 1982, 40, 666-669;
- (1982) Acta Chimica Sinica (Huaxue Xuebao) , vol.40 , pp. 666-669
- Zhou, W.¹ Zhuang, Z.² Wang, Z.³

30
- 0005143957
- e) W. Zhou, Z. Wang, Z. Hao, R. Fei, Z. Zhuang, Acta Chimica Sinica (Huaxue Xuebao) 1985, 43, 168-173.
- (1985) Acta Chimica Sinica (Huaxue Xuebao) , vol.43 , pp. 168-173
- Zhou, W.¹ Wang, Z.² Hao, Z.³ Fei, R.⁴ Zhuang, Z.⁵

31
- 0037020443
- N. Shimizu, H. Akita, T. Kawamata, Tetrahedron Asymmetry 2002, 13, 2123-2134.
- (2002) Tetrahedron Asymmetry , vol.13 , pp. 2123-2134
- Shimizu, N.¹ Akita, H.² Kawamata, T.³

32
- 33845279247
- H. Hagiwara, H. Uda, J. Org. Chem. 1988, 53, 2308-2311.
- (1988) J. Org. Chem. , vol.53 , pp. 2308-2311
- Hagiwara, H.¹ Uda, H.²

33
- 0030593621
- T. Shimizu, S. Hiranuma, T. Nakata, Tetrahedron Lett. 1996, 37, 6145-6148.
- (1996) Tetrahedron Lett. , vol.37 , pp. 6145-6148
- Shimizu, T.¹ Hiranuma, S.² Nakata, T.³

34
- 0000507702
- Z. G. Hajos, D. R. Parrish, Org. Synth. Coll. Vol. 7 1990, 363-368.
- (1990) Org. Synth. Coll. Vol. 7 , vol.7 , pp. 363-368
- Hajos, Z.G.¹ Parrish, D.R.²

35
- 0010632154
- S. Ramachandran, M. S. Newman, Org. Synth. Coll. Vol. 5 1973, 486-489.
- (1973) Org. Synth. Coll. Vol. 5 , vol.5 , pp. 486-489
- Ramachandran, S.¹ Newman, M.S.²

36
- 0033728398
- Z.-L. Wei, Z.-Y. Li, G.-Q. Lin, Synthesis 2000, 1673-1676.
- (2000) Synthesis , pp. 1673-1676
- Wei, Z.-L.¹ Li, Z.-Y.² Lin, G.-Q.³

37
- 0033067092
- E. Emori, T. Iida, M. Shibasaki, J. Org. Chem. 1999, 64, 5318-5320.
- (1999) J. Org. Chem. , vol.64 , pp. 5318-5320
- Emori, E.¹ Iida, T.² Shibasaki, M.³

38
- 84985738428
- P. E. Eaton, P. G. Jobe, Synthesis 1983, 796-797.
- (1983) Synthesis , pp. 796-797
- Eaton, P.E.¹ Jobe, P.G.²

39
- 33847803888
- Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1612-1615.
- (1974) J. Org. Chem. , vol.39 , pp. 1612-1615
- Hajos, Z.G.¹ Parrish, D.R.²

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