Chemoenzymatic synthesis of enantiopure (+)-presqualene diphosphate analogues

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

Volumn 38, Issue 9, 1999, Pages 1011-1014

  Banwell, Martin G ^a   Forman, Grant S ^a   Hockless, David C R ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CATECHOL DERIVATIVE; CYCLOPROPANE; PRESQUALENE DIPHOSPHATE; SQUALENE DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOMER; HOST RESISTANCE; HYPERCHOLESTEROLEMIA; INFLAMMATION; OXIDATION; SYNTHESIS;

EID: 0033513339     PISSN: 03764699     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (37)

1. Levy B D, Petasis N A & Serhan C N, Nature, 389, 1997, 985.
2. Jarstfer M B, Blagg B S J, Rogers D H & Poulter C D, J Am Chem Soc, 118, 1996, 13089 and references cited therein.
3. For excellent reviews of this area see: (a) Poulter C D, Acc Chem Res, 23, 1990, 70.
4. (b) Abe I, Tomesch J C, Wattanasin S & Prestwich G D, Nat Prod Rep, 1994, 279.
5. See, for example: (a) Ratemi E S, Dolence J M, Poulter C D & Vederas J C, J Org Chem, 61, 1996, 6296.
6. (b) Mu Y-Q, Gibbs R A, Eubanks L M & Poulter C D, J Org Chem, 61, 1996, 8010.
7. (c) Cassidy P B & Poulter C D, J Am Chem Soc, 118, 1996, 8761.
8. (a) Coates R M & Robinson W H, J Am Chem Soc, 93, 1971, 1785.
9. (b) Altman L R, Kowerski R C & Rilling H C, J Am Chem Soc, 93, 1971, 1782.
10. (c) Campbell R V M, Crombie L & Pattenden G, J Chem Soc, Chem Commun, 1971, 218.
11. (d) Altman L J, Kowerski R C & Laungani D R, J Am Chem Soc, 100, 1978, 6174.
12. Rogers D H, Yi E C & Poulter C D, J Org Chem, 60, 1995, 941.
13. For useful reviews of this topic see: (a) Charette A B & Marcoux J-F, Synlett, 1995, 1197.
14. (b) Denmark S E. Christenson B L, O'Connor S P & Murase N, Pure Appl Chem, 68, 1996, 23.
15. (c) Reissig H-U, Angew Chem Int Ed Engl, 35, 1996, 971.
16. (d) Singh V K, DattaGupta A & Sekar G, Synthesis, 1997, 137.
17. (e) Wills M, J Chem Soc, Perkin Trans 1, 1998, 3101.
18. Banwell M G & Forman G S, J Chem Soc, Perkin Trans 1, 1996, 2565.
19. For reviews on the applications of cw-1,2-dihydrocatechols in synthesis see: (a) Widdowson D A, Ribbons D W & Thomas S D, Janssen Chimica Acta, 1990, 3.
20. (b) Carless H A J, Tetrahedron Asym, 3, 1992, 795.
21. (c) Brown S M & Hudlicky T, In: Organic Synthesis: Theory and Applications, Vol. 2, Edited by T Hudlicky (JAI: Greenwich, CT), 1993, p. 113.
22. (d) Hudlicky T & Reed J W, In: Advances in Asymmetric Synthesis Vol. 1, edited by A Hassner (JAI: Greenwich, CT) 1995, p. 271.
23. (e) Hudlicky T & Thorpe A J, Chem Commun, 1996, 1993.
24. All optical rotations were determined in chloroform solution at 20°C.
25. (a) Hudlicky T, Boros C C & Boros E E, Sxynthesis, 1992, 174.
26. (b) Gonzalez D, Schapiro V, Seoane G, Hudlicky T & Abboud K, J Org Chem, 62, 1997, 1194.
27. All new and stable compounds had spectroscopic data [IR, UV, NMR, mass spectrum] consistent with the assigned structure. Satisfactory combustion and/or high resolution mass spectra analytical data were obtained for new compounds and/or suitable derivatives.
28. Doyle M P, van Leusen D & Tamblyn W H, Synthesis, 1981, 787.
29. Banwell M G & Reum M E, In: Advances in Strain in Organic Chemistry; Vol. 1, edited by B Halton (JAI: Greenwich CT) 1991, p. 19 and references cited therein.
30. Jackman L M & Sternhell S, Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd edition (Pergamon Press, Oxford) 1969, p. 286.
31. -1, semi-empirical absorption correction; 1765 unique data (2 Θ max = 120.0°), 1631 with I > 3σ(I); R = 0.036, wR = 0.056, GOF = 2.43.
32. 1,3 = 8.9 Hz}.
33. Coates R M, Ley D A & Cavender P L, J Org Chem, 43, 1978, 4915.
34. 13C NMR chemical shift arguments including ones similar to those enunciated by Bohlmann (Bohlmann F, Zeisberg R & Klein E, Org Mag Res, 7, 1975, 426) and Whiting (Crombie L, King R W & Whiting D A, J Chem Soc, Perkin Trans 1, 1975 913). In structures 12-27, the even-numbered ones possess the E-configuraton about the arrowed C=C bond while the odd-numbered ones possess the Z-configuration about the same double-bond (cf. Scheme I).
35. 13C NMR chemical shift arguments including ones similar to those enunciated by Bohlmann (Bohlmann F, Zeisberg R & Klein E, Org Mag Res, 7, 1975, 426) and Whiting (Crombie L, King R W & Whiting D A, J Chem Soc, Perkin Trans 1, 1975 913). In structures 12-27, the even-numbered ones possess the E-configuraton about the arrowed C=C bond while the odd-numbered ones possess the Z-configuration about the same double-bond (cf. Scheme I).
36. (a) Capson T L, Thompson M D, Dixit M, Gaughan R G & Poulter C D, J Org Chem, 53, 1988, 5903.
37. (b) Poulter C D, Capson T L, Thompson M D & Bard R S, J Am Chem Soc, 111, 1989, 3734.