Enantioselective synthesis of cis-7-methoxy-calamenene via Claisen rearrangement of an enzymatically resolved allyl alcohol

Tetrahedron Asymmetry

Volumn 15, Issue 2, 2004, Pages 335-340

  Brenna, Elisabetta ^a   Dei Negri, Claudia ^a   Fuganti, Claudio ^a   Gatti, Francesco G ^a   Serra, Stefano ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

7 METHOXYCALAMENENE; ALKENE DERIVATIVE; ALLYL ALCOHOL; BENZILIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CIS ISOMER; CLAISEN CONDENSATION; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ACTIVITY; PRIORITY JOURNAL; STEREOCHEMISTRY; VILSMEIER HAACK REACTION;

EID: 0347594420     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.11.021     Document Type: Article

References (42)

1. Mulzer J., Altenbach H.-J., Braun M., Krohn K., Reissig H.-U. Organic Synthesis Highlights. 1st ed. 1990;VCH, Berlin.
2. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. 1999;Springer, Heidelberg, Germany. Chapter 5, p 121.
3. Hayashi T. Synlett. 2001;879.
4. Takaya Y., Ogasawara M., Hayashi T., Sakai M., Miyaura N. J. Am. Chem. Soc. 120:1998;5579.
5. Takaya Y., Ogasawara M., Hayashi T. Tetrahedron Lett. 39:1998;8479.
6. Magnus M., Magnus P. Nature. 385:1997;799.
7. Myers A.G., Yang B.H., Chen H., McKistry L., Kopecky D.J., Gleason J.L. J. Am. Chem. Soc. 119:1997;6496.
8. Pippel D.J., Curtis M.D., Du H., Beak P. J. Org. Chem. 63:1998;2.
9. Geller T., Schmalz H.G., Bats J. Tetrahedron Lett. 39:1998;1537.
10. Hoppe D., Hense T. Angew. Chem., Int. Ed. 36:1997;2283.
11. Beak P., Basu A., Gallagher D.J., Park Y.S., Thayumanavan S. Acc. Chem. Res. 29:1996;552.
12. Ruano J.L.G., Carreno M.C., Toledo M.A., Aguirre J.M., Aranda M.T., Fischer J. Angew. Chem., Int. Ed. 39:2000;2736.
13. Gathergood N., Zhuang W., Jørgensen K.A. J. Am. Chem. Soc. 122:2000;12517.
14. Saaby S., Fang X.M., Gathergood N., Jørgensen K.A. Angew. Chem., Int. Ed. 29:2000;4114.
15. Paras N.A., MacMillan D.W.C. J. Am. Chem. Soc. 124:2002;7894.
16. Hirai G., Koizumi Y., Moharram S.M., Oguri H., Hirama M. Org. Lett. 4:2002;1627.
17. Corey E.J., Guzman-Perez A. Angew. Chem., Int. Ed. 37:1998;388.
18. Tanaka K., Qiao S., Tobisu M., Lo M.M.-C., Fu G.C. J. Am. Chem. Soc. 122:2000;9870.
19. For a book or review article on Claisen rearrangement, see: Ziegler F.E. Chem. Rev. 88:1988;1423.
20. Wipf P. Trost M.B., Fleming I. Comprehensive of Organic Chemistry. Vol. 5:1991;Pergamon, New York.
21. For example, see: Brenna E., Carraccia N., Fuganti C., Fuganti D., Grasselli P. Tetrahedron: Asymmetry. 8:1997;3801.
22. Brenna E., Fuganti C., Grasselli P., Serra S. Eur. J. Org. Chem. 2001;1349.
23. Brenna E., Fuganti C., Gatti F.G., Passoni M., Serra S. Tetrahedron: Asymmetry. 14:2003;2401.
24. The cis-7-methoxy-calamenene has been isolated from a cell culture of the liverwort: Nabeta K., Katayama K., Nakagavara S., Katoh K. Phytochemistry. 32:1993;117.
25. For a racemic synthesis of 1 , see: Alexander J., Rao G.S.K. Tetrahedron. 27:1971;645.
26. For a diastereoselective synthesis of 1 , see: Uemura M., Isobe K., Take K., Hayashi Y. J. Org. Chem. 48:1983;3855.
27. For recent examples of benzoannulation reactions applied for the construction of chiral tetrahydronaphthalene derivatives, see: Corey E.J., Palani A. Tetrahedron Lett. 38:1997;2397.
28. Haddad N., Salman H. Tetrahedron Lett. 38:1997;6087.
29. Brenna E., Fuganti C., Serra S. Synlett. 1998;365.
30. Kocienski P.J., Pontiroli A., Qun L. J. Chem. Soc., Perkin Trans. 1. 19:2001;2356.
31. Nakashima K., Imoto M., Sono M., Tori M., Nagaschima F., Asakawa Y. Molecules. 7:2002;517.
32. Funk R.L., Vollhardt K.P.C. Chem. Soc. Rev. 9:1980;41.
33. Titze L.F., Raschke T. Synlett. 38:1997;597.
34. Knoelker H.-J., Ahrens B., Gonser P., Heininger M., Jones P.G. Tetrahedron. 15:2000;2259.
35. Enantioselective reduction of ketone 2 with oxaborolidines gives (R)-alcohol with 97% ee, see: Corey E.J., Helal C.J. Tetrahedron Lett. 36:1995;9153.
36. For dynamic kinetic resolutions of 3 or simple resolutions on similar substrates, see: Lee D., Huh E.A., Kim M.-J., Jung H.M., Koh J.H., Park J. Org. Lett. 2000;2377.
37. Johnson W.S., Werthemann L., Bartlett W.R., Brocksom T.J., Li T.-T. J. Am. Chem. Soc. 92:1970;741.
38. Bohlmann F., Mailahn W. Chem. Ber. 114:1981;1091.
39. Ho T.-L., Y P.-F. Tetrahedron Lett. 51:1991;181.
40. Downie I.M., Earle M.J., Heaney H., Shuhaibar K.F. Tetrahedron. 49:1993;4015.
41. Bordoloi M., Shukla V.S., Nath S., Sharma R.P. Phytochemistry. 28:1989;2007.
42. Cervinka Z. Chem. 11:1971;109.