Parallel kinetic resolution of propargyl ketols: formal synthesis of (+)-bakkenolide A

Tetrahedron

Volumn 64, Issue 20, 2008, Pages 4627-4636

  Kato, Keisuke ^a   Motodate, Satoshi ^a   Takaishi, Satoshi ^a   Kusakabe, Taichi ^a   Akita, Hiroyuki ^a  

^a TOHO UNIVERSITY   (Japan)

Author keywords

Bisoxazoline; Carbonylation; Hydrindane; Palladium; Parallel kinetic resolution

Indexed keywords

ALCOHOL DERIVATIVE; BAKKENOLIDE A; BUTYROLACTONE; ESTER DERIVATIVE; KETONE DERIVATIVE; PALLADIUM; PROPYLENE; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; ENANTIOMER; KINETICS; PRIORITY JOURNAL; SYNTHESIS;

EID: 41549150620     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.101     Document Type: Article

References (57)

1. Tsuji J. Palladium Reagents and Catalysts (1995), John Wiley and Sons, Chichester, UK p 19
2. Stille J.K. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 4 (1991), Pergamon, New York, NY 913
3. For recent reviews:
4. Nakamura I., and Yamamoto Y. Chem. Rev. 104 (2004) 2127
5. Zeni G., and Larock R.C. Chem. Rev. 104 (2004) 2285
6. Alonso F., Beletskaya I.P., and Yus M. Chem. Rev. 104 (2004) 3079
7. Tietze L.F., Ila H., and Bell H.P. Chem. Rev. 104 (2004) 3453
8. Soderberg B.C.G. Coord. Chem. Rev. 248 (2004) 1085
9. Vizer S.A., Yerzhanov K.B., Quntar A.A.A.A., and Dembitsky V.M. Tetrahedron 60 (2004) 5499
10. Muzart J. Tetrahedron 61 (2005) 5955
11. Hosokawa T., Uno T., Inui S., and Murahashi S.-I. J. Am. Chem. Soc. 103 (1981) 2318
12. Hosokawa T., Yamanaka T., Itotani M., and Murahashi S.-I. J. Org. Chem. 60 (1995) 6159
13. Ukaji Y., Miyamoto M., Mikuni M., Takeuchi S., and Inomata K. Bull. Chem. Soc. Jpn. 69 (1996) 735
14. Imada Y., Fujii M., Kubota Y., and Murahashi S.-I. Tetrahedron Lett. 38 (1997) 8227
15. Uozumi Y., Kato K., and Hayashi T. J. Am. Chem. Soc. 119 (1997) 5063
16. Okuro K., Kai H., and Alper H. Tetrahedron: Asymmetry 8 (1997) 2307
17. El-qisairi A., Hamed O., and Henry P.-M. J. Org. Chem. 63 (1998) 2790
18. Arai M.A., Kuraishi M., Arai T., and Sasai H. J. Am. Chem. Soc. 123 (2001) 2907
19. El-qisairi A., Qaseer A.-H., and Henry M.-P. Tetrahedron Lett. 43 (2002) 4231
20. Overman L.E., and Remarchuk T.P. J. Am. Chem. Soc. 124 (2002) 12
21. Yokota T., Sakaguchi S., and Ishii Y. J. Org. Chem. 67 (2002) 5005
22. Girones J., Duran J., Polo A., and Real J. Chem. Commun. (2003) 1776
23. Shinohara T., Arai M.A., Wakita K., Arai T., and Sasai H. Tetrahedron Lett. 44 (2003) 711
24. Muthiah C., Arai M.A., Shinohara T., Arai T., Takizawa S., and Sasai H. Tetrahedron Lett. 44 (2003) 5201
25. Trend R.M., Ramtohul Y.K., Ferreira E.M., and Stoltz B.M. Angew. Chem., Int. Ed. 42 (2003) 2892
26. Takizawa S., Honda Y., Arai M.A., Kato T., and Sasai H. Heterocycles 60 (2003) 2551
27. Wakita K., Arai M.A., Kato T., Shinohara T., and Sasai H. Heterocycles 62 (2004) 831
28. Stahl S.S. Angew. Chem., Int. Ed. 43 (2004) 3400
29. Alper H., and Dong C. Tetrahedron: Asymmetry 15 (2004) 35
30. Stoltz B.M. Chem. Lett. 33 (2004) 362
31. Hayashi T., Yamasaki K., Mimura M., and Uozumi Y. J. Am. Chem. Soc. 126 (2004) 3036
32. Trend R.M., Ramtohul Y.K., and Stoltz B.M. J. Am. Chem. Soc. 127 (2005) 17778
33. Tietze L.F., Sommer K.M., Zinngrebe J., and Stecker F. Angew. Chem., Int. Ed. 44 (2005) 257
34. Wang F., Zhang Y.J., Yang G., and Zhang W. Tetrahedron Lett. 48 (2007) 4179
35. Kato K., Tanaka M., Yamamoto Y., and Akita H. Tetrahedron Lett. 43 (2002) 1511
36. Kato K., Matsuba C., Kusakabe T., Takayama H., Yamamura S., Mochida T., Akita H., Peganova T.A., Vologdin N.V., and Gusev O.V. Tetrahedron 62 (2006) 9988
37. Kato K., Tanaka M., Yamamura S., Yamamoto Y., and Akita H. Tetrahedron Lett. 44 (2003) 3089
38. Kusakabe T., Kato K., Takaishi S., Yamamura S., Mochida T., Akita H., Peganova T.A., Vologdin N.V., and Gusev O.V. Tetrahedron 64 (2008) 319
39. Pd(0) catalyzed intramolecular asymmetric hydroamination of alkynes. Lutete L.M., Kadota I., and Yamamoto Y. J. Am. Chem. Soc. 126 (2004) 1622
40. Reaction of 4-yne-1-ols:
41. Kato K., Nishimura A., Yamamoto Y., and Akita H. Tetrahedron Lett. 42 (2001) 4203
42. Takayama H., Kato K., and Akita H. Eur. J. Org. Chem. (2006) 644
43. Reaction of 4-yne-1-ones:
44. Kato K., Yamamoto Y., and Akita H. Tetrahedron Lett. 43 (2002) 4915
45. Reaction of propargyl acetates:
46. Kato K., Yamamoto Y., and Akita H. Tetrahedron Lett. 43 (2002) 6587
47. Kato K., Nouchi H., Ishikura K., Takaishi S., Motodate S., Tanaka H., Okudaira K., Mochida T., Nishigaki R., Shigenobu K., and Akita H. Tetrahedron 62 (2006) 2545
48. Kato K., Teraguchi R., Yamamura S., Mochida T., Akita H., Peganova T.A., Vologdin N.V., and Gusev O.V. Synlett (2007) 638
49. Honda T., Sano N., and Kanai K. Heterocycles 41 (1995) 425
50. Tanaka K., and Fu G.C. J. Am. Chem. Soc. 125 (2003) 8078 and references cited therein
51. Maeyama K., and Iwasawa N. J. Am. Chem. Soc. 120 (1998) 1928
52. Bourgeois D., Prunet J., Pancrazi A., Prangé T., and Lallemand J.-Y. Eur. J. Org. Chem. (2000) 4029
53. Because the mixture of 12 and 13 was difficult to separate, separation was carried out after conversion of 12 to 14.
54. Brocksom T.J., Coelho F., Depres J.-P., Greene A.E., Freire de lima M.E., Hamelin O., Hartmann B., Kanazawa A.M., and Wang Y. J. Am. Chem. Soc. 124 (2002) 15313
55. Evans D.A., Sims C.L., and Andrews G.C. J. Am. Chem. Soc. 99 (1977) 5453
56. Greene A.E., Coelho F., Depres J.-P., and Brocksom T.J. Tetrahedron Lett. 29 (1988) 5661
57. (-)-7-Epibakkenolide-A was synthesized from (+)-20. Srikrishna A., and Reddy T.J. Tetrahedron 54 (1998) 11517