A mild biosynthesis of lactones via enantioselective hydrolysis of hydroxynitriles

Tetrahedron Asymmetry

Volumn 18, Issue 16, 2007, Pages 1888-1892

  Pollock, Julie A ^a   Clark, Karen M ^a   Martynowicz, Bethany J ^a   Pridgeon, Matthew G ^a   Rycenga, Matthew J ^a   Stolle, Kristen E ^a   Taylor, Stephen K ^a  

^a HOPE COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE; NITRILASE; NITRILE; PHEROMONE;

ARTICLE; BIOCATALYST; BIOSYNTHESIS; ENANTIOSELECTIVITY; HYDROLYSIS; PRIORITY JOURNAL; SYNTHESIS;

EID: 34548543507     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.07.034     Document Type: Article

References (26)

1. Brown H.C., KulKarni S.V., and Racherla U.S. J. Org. Chem. 59 (1994) 365-369
2. For representative examples, see:. Prout F.S., Hartman R.J., Huang E.P.-Y., Korpics C.J., and Tichelaar G.R. Organic Syntheses (1963), Wiley, New York Collect. Vol. IV, pp 93-98
3. Allen C.F.H., and Johnson H.B. Organic Syntheses (1963), Wiley, New York Collect. Vol. IV, pp 804-806
4. McGuire M.A., Sorenson E., Owings R.W., Resnick T.M., Rox M., and Baine N.H. J. Org. Chem. 59 (1994) 6683-6686
5. Pirkle W.H., and Adams P.E. J. Org. Chem. 44 (1979) 2169-2175
6. Gopalan A., Lucero R., Jacobs H., and Berryman K. Synth. Commun. 21 (1991) 1321-1329
7. Taylor S.K., Chmiel N.H., Simons L.J., and Vyvyan J.R. J. Org. Chem. 61 (1996) 9084-9085
8. Robertson D.E., Chaplin J.A., DeSantis G., Podar M., Madden M., Chi E., Richardson T., Milan A., Miller M., Weiner D.P., Wong K., McQuaid J., Farwell B., Preston L.A., Tan X., Snead M.A., Keller M., Mathur E., Kretz P.L., Burk M.J., and Short J.M. Appl. Environ. Microbiol. 70 (2004) 2429-2436 and references cited therein
9. DeSantis G., Zhu Z., Greenburg W.A., Wong K., Chaplin J., Hanson S.R., Farwell B., Nicholson L.W., Rand C.L., Weiner D.P., Robertson D.E., and Burk M.J. J. Am. Chem. Soc. 124 (2002) 9024-9025
10. Taylor S.K., DeYoung D., Simons L.J., Vyvyan J.R., Wemple M.A., and Wood N.K. Synth. Commun. 28 (1998) 1691-1701 Make sure that the final neutralization of the enolate reaction product is done at -15 °C
11. Paddon-Jones G.C., Moore C.J., Bracknell D.J., Konig W.A., and Kitching W. Tetrahedron Lett. 38 (1997) 3479-3482
12. * (1 - ee))) Faber, K. Biotransformations in Organic Chemistry; New York, 1995; pp 32-40; see pp 124-133 for nitrile hydrolyses.
13. Mori K. Tetrahedron 45 (1989) 3233-3298
14. Mayaux J.-F., Cerbelaud E., Soubrier F., Yeh P., Blanche F., and Pétré D. J. Bacteriol. 173 (1991) 6694-6704
15. Utaka M., Watabu H., and Takeda A. J. Org. Chem. 52 (1987) 4363-4368
16. Chattopadhyay S., Mamdapur V.R., and Chadha M.S. Tetrahedron 46 (1990) 3667-3672
17. Taylor S.K. Tetrahedron 56 (2000) 1149-1163
18. Taylor S.K., Fried J.A., Grassl Y.N., Marolewski A.E., Pelton E.A., Poel T.J., Rezanka D.S., and Whittaker M.R. J. Org. Chem. 58 (1993) 7304-7307
19. Taylor S.K., Arnold C.R., Gerds A.T., Ide N.D., Law K.M., Kling D.L., Pridgeon M.G., Simons L.J., Vyvyan J.R., Yamaoka J.S., Liao M.-K., and Goyne T.E. Tetrahedron: Asymmetry 15 (2004) 3819-3821
20. Shaw J.E., and Kunerth D.C. J. Org. Chem. 39 (1974) 1968-1970
21. Zhou J.J.P., Zhong B., and Silverman R.B. J. Org. Chem. 60 (1995) 2261-2262
22. Barleunga J., Fernandez J.R., Rubiera C., and Yus M. J. Chem. Soc., Perkin Trans. 1 (1988) 3113-3117
23. Wade P., and Pillay M.K. J. Org. Chem. 46 (1981) 5425-5427
24. Klempier N., de Raadt A., Faber K., and Griengl H. Tetrahedron Lett. 32 (1991) 341-344
25. de Raadt A., Klempier N., Faber K., and Griengl H. J. Chem. Soc., Perkin Trans. 1 (1992) 137-140
26. Curran D.P., Scanga S.A., and Fenk C. J. Org. Chem. 49 (1984) 3474-3478