Pd catalyzed kinetic resolution of conduritol B. Asymmetric synthesis of (+)-cyclophellitol

Tetrahedron Letters

Volumn 40, Issue 2, 1999, Pages 219-222

  Trost, B M ^a   Hembre, E J ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONDURITOL B; CYCLOPHELLITOL; GLYCOSIDASE INHIBITOR; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENZYME INHIBITION; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033534643     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02274-6     Document Type: Article

References (28)

1. Atsumi S. Umezawa K. Iinuma H. Naganawa H. Nakamura H. Iitaka Y. Takeuchi T. J. Antibiot. 43 1990 49
2. Atsumi S. Iinuma H. Nosaka C. Umezawa K. J. Antibiot. 43 1990 1579
3. Tatsuta K. Niwata Y. Umezawa K. Toshima K. Nakata M. Carbohydrate Res. 222 1991 189
4. Sato K.I. Bokura M. Moriyama H. Igarashi T. Chem. Lett. 37 1994
5. McDevitt R.E. Fraser-Reid B. J. Org. Chem. 59 1994 3250
6. Jung M.E. Choe S.W.T. J. Org. Chem. 60 1995 3280
7. Le Tellier P. Ralainairina R. Beaupère D. Uzan R. Synthesis 1997 925
8. Ziegler F.E. Wang Y. J. Org. Chem. 63 1998 426
9. Akiyama T. Shima H. Ohnari M. Okazaki T. Ozaki S. For non-carbohydrate enantiomerically pure precursors, see: Bull. Chem. Soc. Jpn. 66 1993 3760
10. Shing T.K.M. Tai V.W.F. J. Chem. Sco. Perkin Trans. I 1994 2017
11. Schlessinger R.H. Bergstrom C.P. J. Org. Chem. 60 1995 16
12. Moritz V. Vogel P. For racemic syntheses, see: Tetrahedron Lett. 33 1992 5243
13. Acena J.L. Arjona O. Plumet J. J. Org. Chem. 62 1997 3360
14. Guo Z.-X. Haines A.H. Pyke S.M. Pyke S.G. Taylor R.J.K. Carbohydr. Res. 264 1994 147
15. For some recent asymmetric syntheses of conduritol B from the chiral pool, see: Miyazaki H. Kobayashi Y. Shiozaki M. Ando O. Nakajima M. Hanzawa H. Haruyama H. J. Org. Chem. 60 1995 6103
16. Sato K.I. Bokura M. Taniguchi M. Bull. Chem. Soc. Jpn. 67 1994 1633
17. Augy-Dorey S. Barton D.H.R. Géro S.D. Quiclet-Sire B. Sagnard I. Chem. Commun. 1993 960
18. For asymmetric syntheses of either enantiomer of conduritol B from L-quebrachitol, see: Akiyama T. Shima H. Ohnari M. Okazaki T. Ozaki S. Bull. Chem. Soc. Jpn. 66 1993 3760
19. Paulsen H. von Deyn W. Annalen 1987 133
20. For resolutions towards conduritol B, see: Innes J.E. Edwards P.J. Ley S.V. J. Chem. Soc. Perkin Trans. I 1997 795
21. Yu L. Cabrera R. Ramirez J. Malinovskii V.A. Brew K. Wang P.G. Tetrahedron Lett. 36 1995 2897
22. Le Drian C. Vionnet J.P. Vogel P. Helv. Chim. Acta 73 1990 161
23. Trost B.M. Van Vranken D.L. Chem. Rev. 96 1996 395
24. Trost B.M. Van Vranken D.L. Bingel C. J. Am. Chem. Soc. 114 1992 9327
25. Trost B.M. Acc. Chem. Res. 1996
26. Trost B.M. Organ M.G. J. Am. Chem. Soc. 116 1994 10320
27. Still W.C. Mitra A. J. Am. Chem. Soc. 100 1978 1927
28. After initial submission of this paper, we became aware of an alternative cleavable pivalate unit that required a hydroboration as one step of the cleavage protocol, see Crimmins M.T. Carroll C.A. Wells A.J. Tetrahedron Lett. 39 1998 7005