On the synthesis of cepacin A

Tetrahedron

Volumn 63, Issue 23, 2007, Pages 4887-4906

  Tang, Chao Jun ^a   Wu, Yikang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Allenes; Antibiotics; Diynes; Epoxides; Lactones

Indexed keywords

ACETONE; ALCOHOL; ALDEHYDE; ALLENE DERIVATIVE; ANTIINFECTIVE AGENT; ARABINOSE; CARBONYL DERIVATIVE; CEPACIN A; EPOXIDE; LACTONE; THIOACETALDEHYDE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; BURKHOLDERIA CEPACIA; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; DESILYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERISM; NUCLEAR MAGNETIC RESONANCE; OXIDATION; PRIORITY JOURNAL; REDUCTION; SONOGASHIRA REACTION;

EID: 34247560216     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.144     Document Type: Article

References (54)

1. Parker W.L., Rathnum M.L., Seiner V., Trejo W.H., Principe P.A., and Sykes R.B. J. Antibiot. 37 (1984) 431-440
2. Bu'Lock J.D., Jones E.R.H., and Leeming P.R. J. Chem. Soc. (1955) 4270-4276
3. Bu'Lock J.D., Jones E.R.H., Leeming P.R., and Thompson J.M. J. Chem. Soc. (1956) 3767-3771
4. Lowe G. J. Chem. Soc., Chem. Commun. (1965) 411-413
5. Brewster J.H. In: Allinger N.L., and Eliel E.L. (Eds). Topics in Stereochemistry Vol. 2 (1967), John Wiley and Sons, New York, NY 1-72
6. For a communication on part of the present work, see:. Tang C.-J., and Wu Y.-K. Helv. Chim. Acta 87 (2004) 667-673
7. Schoerkhuber W., and Zbiral E. Liebigs Ann. Chem. (1980) 1455-1469
8. Ireland R.E., Countney L., and Fitzsimmons B.J. J. Org. Chem. 48 (1983) 5186-5198
9. Liu H.-J., Yip J., and Shia K.-S. Tetrahedron Lett. 38 (1997) 2253-2256
10. Kiso M., and Hasegawa A. Carbohydr. Res. 52 (1976) 95-101
11. Cason J. Org. Synth. Coll. Vol. 3 (1955) 169-171
12. Ronald R.C., and Wheeler C.J. J. Org. Chem. 48 (1983) 138-139
13. Macdonald S.F. Can. J. Chem. 52 (1974) 3257-3258
14. Enholm E.J., and Trivellas A. J. Am. Chem. Soc. 111 (1989) 6463-6465
15. White J.D., and Jensen M.S. J. Am. Chem. Soc. 117 (1995) 6224-6233
16. Dondoni A., Marra A., and Merino P. J. Am. Chem. Soc. 116 (1994) 3324-3336
17. Luche J.-L. J. Am. Chem. Soc. 100 (1978) 2226-2227
18. Gemal A.L., and Luche J.-L. J. Am. Chem. Soc. 103 (1981) 5454-5459
19. Xiao X., and Bai D. Synlett (2001) 535-537
20. Murugensan V., and Pandurangan A. Indian J. Chem. 31B (1992) 377-378
21. For another failure with QFC oxidation, see:. Wu Y.-K., Shen X., Yang Y.-Q., Hu Q., and Huang J.-H. J. Org. Chem. 69 (2004) 3857-3865
22. Kutterer K.M.K., and Just J. Heterocycles 51 (1999) 1409-1420
23. Miyashita M., Yoshikoshi A., and Grieco P.A. J. Org. Chem. 42 (1977) 3772-3774
24. Sterzycki R. Synthesis (1979) 724-725
25. Frigerio M., and Santagostino M. Tetrahedron Lett. 35 (1994) 8019-8022
26. De Munari S., Frigerio M., and Santagostino M. J. Org. Chem. 61 (1996) 9272-9279
27. Frigerio M., Santagostino M., and Sputore S. J. Org. Chem. 64 (1999) 4537-4538
28. Corey E.J., and Suggs J.W. Tetrahedron Lett. (1975) 2647-2650
29. Piancatelli G., Scettri A., and D'Auria M. Synthesis (1982) 245-258
30. Dess D.B., and Martin J.C. J. Org. Chem. 48 (1983) 4155-4156
31. Dess D.B., and Martin J.C. J. Am. Chem. Soc. 113 (1991) 7277-7278
32. Ireland R.E., and Liu L.-B. J. Org. Chem. 58 (1993) 2899
33. Stevenson P.J., Treacy A.B., and Nieuwenhuyzen M. J. Chem. Soc., Perkin Trans. 2 (1997) 589-591
34. Parikh J.R., and Doering W.E. J. Am. Chem. Soc. 89 (1967) 5505-5507
35. Tidwell T.T. Org. React. 39 (1990) 297-572 (a review)
36. Coery E.J., and Erickson B.W. J. Org. Chem. 19 (1971) 3553-3560
37. Armstrong R.W., and Teegarden B.R. J. Org. Chem. 57 (1992) 915-922
38. Shi X.-X., and Wu Q.-Q. Synth. Commun. 30 (2000) 4081-4086
39. Loudon G.M., Radhakrishna A.S., Almond M.R., Blodgett J.K., and Boutin R.H. J. Org. Chem. 49 (1984) 4272-4276
40. Stork G., and Zhao K. Tetrahedron Lett. 30 (1989) 287-290
41. Nicolaou K.C., Bunnage M.E., McGarry D.G., Shi S., Somers P.K., Wallace P.A., Chu X.-J., Agrios K.A., Gunzner J.L., and Yang Z. Chem.-Eur. J. 5 (1999) 599-617
42. Russell G.A., and Ochrymowy L.A. J. Org. Chem. 34 (1969) 3618-3624
43. Corey E.J., Bakshi R.K., and Shibata S. J. Am. Chem. Soc. 109 (1987) 5551-5553
44. Corey E.J., Bakshi R.K., Shibata S., Chen C.-P., and Singh V.K. J. Am. Chem. Soc. 109 (1987) 7925-7926
45. For a recent review:. Corey E.J., and Helal C.J. Angew. Chem., Int. Ed. 36 (1998) 1986-2012
46. The natural cepacin A is a 1:1 mixture at this position. We chose to do asymmetric reduction at this stage purely for facilitating spectral assignment.
47. D'Aniello F., Mann A., Taddei M., and Wermuth C.-G. Tetrahedron Lett. 35 (1994) 7775-7778
48. D'Aniello F., Schoenfelder A., Mann A., and Taddei M. J. Org. Chem. 61 (1996) 9631-9639
49. Bartik B., Dembinski R., Bartik T., Arif A.M., and Gladysz J.A. New J. Chem. 21 (1997) 739-750
50. Jones C.E., Kondrick D.A., and Holmes A.B. Org. Synth. 65 (1987) 52-60
51. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. (1975) 4467-4470
52. Sonogashira K. J. Organomet. Chem. 653 (2002) 46-49 (a review)
53. Andrus M.B., Lepore S.D., and Turner T.M. J. Am. Chem. Soc. 119 (1997) 12159-12169
54. We also tried to use TES in place of TBS as the protecting group, but the removal was just as difficult as the TBS. Interestingly, the corresponding coupling products (with the C-9 OH either TBS- or TES-protected) from TMSC{triple bond, long}CH instead of TMSC{triple bond, long}C-C{triple bond, long}CH could be readily desilylated to obtain the alcohol.