Lipase-mediated resolution of the hydroxy-cyclogeraniol isomers: application to the synthesis of the enantiomers of karahana lactone, karahana ether, crocusatin C and γ-cyclogeraniol

Tetrahedron Asymmetry

Volumn 20, Issue 11, 2009, Pages 1319-1329

  Serra, Stefano ^a   Gatti, Francesco G ^b   Fuganti, Claudio ^b  

^a CNR   (Italy)

^b Dipartimento di Chimica   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXY BETA CYCLOGERANIOL 14; 3 HYDROXY BETA CYCLOGERANIOL 17; 4 HYDROXY BETA CYCLOGERANIOL 19; CIS 2 HYDROXY ALPHA CYCLOGERANIOL 4; CIS 2 HYDROXY GAMMA CYCLOGERANIOL 5; CIS 3 HYDROXY ALPHA CYCLOGERANIOL 7; CIS 4 HYDROXY GAMMA CYCLOGERANIOL 10; CROCUSATIN C; GAMMA CYCLOGERANIOL; GERANIOL; KARAHANA ETHER; KARAHANA LACTONE; TERPENOID; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CRYSTALLIZATION; DRUG DETERMINATION; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; ISOMER; OPTICAL RESOLUTION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 67649408846     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.05.013     Document Type: Article

References (50)

1. Carotenoids Volume 2: Synthesis; Pfander, H.; Britton, G.; Liaaen-Jensen, S., Eds. Birkhäuser Verlag: Basel, 1996.
2. Brenna E., Fuganti C., Serra S., and Kraft P. Eur. J. Org. Chem. (2002) 967-978
3. Pfander H. Pure Appl. Chem. 63 (1991) 23-33
4. Serra S., Fuganti C., and Gatti F.G. Eur. J. Org. Chem. (2008) 1031-1037
5. Brenna E., Fuganti C., Gatti F.G., Perego M., and Serra S. Tetrahedron: Asymmetry 17 (2006) 792-796
6. Serra S., Brenna E., Fuganti C., and Maggioni F. Tetrahedron: Asymmetry 14 (2003) 3313-3319
7. Serra S., and Fuganti C. Helv. Chim. Acta 85 (2002) 2489-2502
8. Barakat A., Fuganti C., Brenna E., and Serra S. Tetrahedron: Asymmetry 19 (2008) 2316-2322
9. Serra S., Barakat A., and Fuganti C. Tetrahedron: Asymmetry 18 (2007) 2573-2580
10. Serra S., Fuganti C., and Brenna E. Helv. Chim. Acta 89 (2006) 1110-1122
11. Serra S., and Fuganti C. Tetrahedron: Asymmetry 17 (2006) 1573-1580
12. Brenna E., Fuganti C., and Serra S. Tetrahedron: Asymmetry 16 (2005) 1699-1704
13. For the previously reported enantioselective syntheses of kaharana lactone and ether see:. Beszant S., Giannini E., Zanoni G., and Vidari G. Tetrahedron: Asymmetry 13 (2002) 1245-1255
14. Galano J.-M., Audran G., and Monti H. Tetrahedron 56 (2000) 7477-7481
15. Gossellin P., Bonfand E., and Maignan C. J. Org. Chem. 61 (1996) 9049-9052
16. Honda T., Satoh M., and Kobayashi Y. J. Chem. Soc., Perkin Trans. 1 (1992) 1557-1558
17. Mori K., and Mori H. Tetrahedron 41 (1985) 5487-5493
18. Li C.-Y., and Wu T.-S. Chem. Pharm. Bull. 50 (2002) 1305-1309
19. For the previously reported enantioselective syntheses of γ-cyclogeraniol see: Ref. 6a and. Tanimoto H., and Oritani H. Tetrahedron 53 (1997) 3527-3536
20. Fehr C., and Galindo J. Helv. Chim. Acta 78 (1995) 539-552
21. Nahmany M., and Melman A. Tetrahedron 61 (2005) 7481-7488
22. Alcaraz L., Harnett J.J., Mioskowski C., Le Gall T., Shin D.-S., and Falck J.R. J. Org. Chem. 60 (1995) 7209-7214
23. Serra S., Fuganti C., and Brenna E. Flavour Frag. J. 22 (2007) 505-511
24. Brenna E., Fuganti C., Ronzani S., and Serra S. Helv. Chim. Acta 84 (2001) 3650-3666
25. Surmatis J.D., Walser A., Gibas J., and Thommen R. J. Org. Chem. 35 (1970) 1053-1056
26. Luparia M., Boschetti P., Piccini F., Porta A., Zanoni G., and Vidari G. Chem. Biodiversity 5 (2008) 1045-1057
27. Ishikawa T., Kadoya R., Arai M., Takahashi H., Kaisi Y., Mizuta T., Yoshikai K., and Saito S. J. Org. Chem. 66 (2001) 8000-8009
28. Roy O., Pattenden G., Pryde D.C., and Wilson C. Tetrahedron 59 (2003) 5115-5121
29. Di Grandi M.J., Jung D.K., Krol W.J., and Danishefsky S.J. J. Org. Chem. 58 (1993) 4989-4992
30. Barton D.H.R., Bashiardes G., and Fourrey J.L. Tetrahedron 44 (1988) 147-162
31. Brooks D.W., Bevinakatti H.S., Kennedy E., and Hathaway J. J. Org. Chem. 50 (1985) 628-632
32. Anies C., Pancrazi A., and Lallemand J.-Y. Bull. Soc. Chim. Fr. 134 (1997) 183-202
33. Gamalevich G.D., and Serebryakov E.P. Russ. Chem. Bull. 46 (1997) 171-183
34. Serebryakov E.P., Gamalevich G.D., Kulcitki V.N., Ungur N.D., and Vlad P.F. Mendeleev Commun. 12 (2002) 59-60
35. Fujiwara N., Kinoshita M., and Akita H. J. Mol. Catal. B: Enzym. 40 (2006) 64-72
36. Dess D.B., and Martin J.C. J. Org. Chem. 48 (1983) 4155-4156
37. For the previously reported enantioselective syntheses of diol 17 and its derivatives see:. Yamano Y., Tode C., and Ito M. J. Chem. Soc., Perkin Trans. 1 (1998) 2569-2581
38. Rüttimann A., and Mayer H. Helv. Chim. Acta 63 (1980) 1456-1466
39. No enantioselective synthesis of this diol has been reported until now.
40. Bovolenta M., Castronovo F., Vadalà A., Zanoni G., and Vidari G. J. Org. Chem. 69 (2004) 8959-8962
41. Although enantioenriched diol 10 was not previously obtained, the (6S)-enantiomer of its TBDPS ether was prepared as described in Ref. 13.
42. Monti H., and Audran G. Mini-Rev. Org. Chem. 2 (2005) 546-564
43. Palombo E., Audran G., and Monti H. Synlett (2005) 2104-2106
44. Brémond P., Audran G., Juspin T., and Monti H. Eur. J. Org. Chem. (2007) 2802-2807
45. Bourdron J., Commeiras L., Audran G., Vanthuyne N., Hubaud J.C., and Parrain J.-L. J. Org. Chem. 72 (2007) 3770-3775
46. Hansen T.M., Florence G.J., Lugo-Mas P., Chen J., Abrams J.N., and Forsyth C.J. Tetrahedron Lett. 44 (2003) 57-59
47. Serra S., and Fuganti C. Helv. Chim. Acta 87 (2004) 2100-2109
48. Chen Q.C., Youn U., Min B.-S., and Bae K. J. Nat. Prod. 71 (2008) 995-999
49. Straubinger M., Jezussek M., Waibel R., and Winterhalter P. J. Agric. Food Chem. 45 (1997) 1678-1681
50. Chapuis C., and Schulte-Elte K.H. Helv. Chim. Acta 78 (1995) 165-176