Synthesis of C18-C28 ketone fragment of micromonospolide B possessing 1,3-diene and 1,3-anti-diol functionalities

Tetrahedron Asymmetry

Volumn 20, Issue 16, 2009, Pages 1864-1870

  Sun, Liang ^a   Wu, Jinlong ^a   Dai, Wei Min ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; EPHEDRINE; KETONE DERIVATIVE; MACROLIDE; MICROMONOSPOLIDE B; PROPIONIC ACID; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL BOND; ENANTIOMER; EPOXIDATION; MICROMONOSPORA; PRIORITY JOURNAL; RING OPENING; STEREOCHEMISTRY;

EID: 69749085400     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.07.042     Document Type: Article

References (55)

1. Ohta E., Ohta S., Kubota N.K., Suzuki M., Ogawa T., Yamasaki A., and Ikegami S. Tetrahedron Lett. 42 (2001) 4181-4197
2. Ohta E., Kubota N.K., Ohta S., Suzuki M., Ogawa T., Yamasaki A., and Ikegami S. Tetrahedron 57 (2001) 8463-8467
3. Dai W.-M., Guan Y., and Jin J. Curr. Med. Chem. 12 (2005) 1947-1993 and the references cited therein
4. Kinashi H., Someno K., Sakaguchi K., Higashijima T., and Miyazawa T. Tetrahedron Lett. 22 (1981) 3857-3860 and 3861-3864
5. Kinashi H., Sakaguchi K., Higashijima T., and Miyazawa T. J. Antibiot. 35 (1982) 1618-1620
6. Kinashi H., Someno K., and Sakaguchi K. J. Antibiot. 37 (1984) 1333-1343
7. Westley J.W., Liu C.-M., Sello L.H., Evans R.H., Troupe N., Blount J.F., Chiu A.M., Todaro L.J., and Miller P.A. J. Antibiot. 37 (1984) 1738-1740
8. Woo J.-T., Shinohara C., Sakai K., Hasumi K., and Endo A. J. Antibiot. 45 (1992) 1108-1116
9. Ishii T., Hida T., Iinuma S., Muroi M., and Nozaki Y. J. Antibiot. 48 (1995) 12-20
10. Omura S., Imamura N., Hinotozawa K., Otoguro K., Lukacs G., Faghih R., Tolmann R., Arison B.H., and Smith J.L. J. Antibiot. 34 (1983) 1783-1786
11. Kumagai K., Fukui A., Tanaka S., Ikemoto M., Moriguchi K., and Nabeshima S. J. Antibiot. 46 (1993) 1139-1144
12. Laakso J.A., Mocek U.M., Van Dun J., Wouters W., and Janicot M. J. Antibiot. 56 (2003) 909-916
13. Werner G., Hagenmaier H., Drautz H., Baumgartner A., and Zähner H. J. Antibiot. 37 (1984) 110-117
14. Werner G., Hagenmaier H., Albert K., Kohlshorn H., and Drautz H. Tetrahedron Lett. 24 (1983) 5193-5196
15. Gilbert S.F. Developmental Biology. 3rd ed. (1991), Sinauer, Sunderland
16. Bowman E.J., Siebers A., and Altendorf K. Proc. Natl. Acad. Sci. U.S.A. 85 (1988) 7972-7976
17. Drose S., and Altendorf K. J. Exp. Biol. 200 (1997) 1-8
18. Yoshimoto Y., Jyojima T., Arita T., Ueda M., Imoto M., Matsumura S., and Toshima K. Bioorg. Med. Chem. Lett. 12 (2002) 2525-2528
19. Bowman B.J., McCall M.E., Baertsch R., and Bowman E.J. J. Biol. Chem. 281 (2006) 31885-31893
20. For reviews, see:. Beutler J.A., and McKee T.C. Curr. Med. Chem. 10 (2003) 787-796
21. Xu J., Cheng T., Feng H.T., Pavlos N.J., and Zheng M.H. Histol. Histopathol. 22 (2007) 443-454
22. Yao G.F., Feng H.T., Cai Y.L., Qi W.L., and Kong K.M. Biochem. Biophys. Res. Commun. 357 (2007) 821-827
23. Farina C., and Gagliardi S. Drug Discovery Today 4 (1999) 163-172
24. Evans D.A., and Calter M.A. Tetrahedron Lett. 34 (1993) 6871-6874
25. (b) Calter, M. A. PhD Thesis; Harvard University, USA, 1993.
26. Toshima K., Jyokaaki T., Yamaguchi H., Murase H., Yoshida T., Mastumura S., and Nakata M. Tetrahedron Lett. 37 (1996) 1069-1072
27. Toshima K., Yamaguchi H., Jyojima T., Noguchi Y., Nakata M., and Mastumura S. Tetrahedron Lett. 37 (1996) 1073-1076
28. Toshima K., Jyojima T., Yamaguchi H., Noguchi Y., Yoshida T., Murase H., Nakata M., and Mastumura S. J. Org. Chem. 62 (1997) 3271-3284
29. Scheidt K.A., Tasaka A., Bannister T.D., Wendt M.D., and Roush W.R. Angew. Chem., Int. Ed. 38 (1999) 1652-1655
30. Scheidt K.A., Bannister T.D., Tasaka A., Wendt M.D., Savall B.M., Fegley G.J., and Roush W.R. J. Am. Chem. Soc. 124 (2002) 6981-6990
31. Hanessian S., Ma J., Wang W., and Gai Y. J. Am. Chem. Soc. 123 (2001) 10200-10206 Correction: Journal Am. Chem. Soc. 2002, 124, 7249
32. Kleinbeck F., and Carreira E.M. Angew. Chem., Int. Ed. 48 (2009) 578-581
33. Lu C., and Shen Y. J. Antibiot. 56 (2003) 415-418
34. Lu C., and Shen Y. J. Antibiot. 57 (2004) 597-600
35. Guan Y., Wu J., Sun L., and Dai W.-M. J. Org. Chem. 72 (2007) 4953-4960
36. For reviews, see:. Schetter B., and Mahrwald R. Angew. Chem., Int. Ed. 45 (2006) 7506-7525
37. Geary L.M., and Hultin P.G. Tetrahedron: Asymmetry 20 (2009) 131-173
38. Abiko A., Liu J.-F., and Masamune S. J. Am. Chem. Soc. 119 (1997) 2586-2587
39. Inoue T., Liu J.-F., Buske D.C., and Abiko A. J. Org. Chem. 67 (2002) 5250-5256
40. Abiko A. Acc. Chem. Res. 37 (2004) 387-395
41. For a review, see:. Hoffmann R.W. Angew. Chem., Int. Ed. Engl. 26 (1987) 489-503
42. Toshima K., Jyojima T., Miyamoto N., Katohno M., Nakata M., and Mastumura S. J. Org. Chem. 66 (2001) 1708-1715 and the references cited therein
43. Paterson I., Doughty V.A., McLeod M.D., and Trieselmann T. Angew. Chem., Int. Ed. 39 (2000) 1308-1312 and the references cited therein
44. Brown H.C., and Bhat K.S. J. Am. Chem. Soc. 108 (1986) 293-294
45. Mukaiyama T., Banno K., and Narasaka K. J. Am. Chem. Soc. 96 (1974) 7503-7509
46. Paterson I., and McLeod M.D. Tetrahedron Lett. 36 (1995) 9065-9068
47. Jin J., Chen Y., Li Y., Wu J., and Dai W.-M. Org. Lett. 9 (2007) 2585-2588
48. Dai W.-M., Feng G., Wu J., and Sun L. Synlett (2008) 1013-1016
49. Dai W.-M., Shi L., and Li Y. Tetrahedron: Asymmetry 19 (2008) 1549-1556
50. Paterson I., Chen D.Y.-K., Coster M.J., Aceña J.L., Bach J., Gibson K.R., Keown L.E., Oballa R.M., Trieselmann T., Wallace D.J., Hodgson A.P., and Norcross R.D. Angew. Chem., Int. Ed. 40 (2001) 4055-4060
51. Yokokawa F., Fujiwara H., and Shioiri T. Tetrahedron 56 (2000) 1759-1775
52. Ley S.V., Norman J., Griffith W.P., and Marsden S.P. Synthesis (1994) 639-666
53. Dess D.B., and Martin J.C. J. Org. Chem. 48 (1983) 4155-4156
54. Meyer S.D., and Schreiber S.L. J. Org. Chem. 59 (1994) 7549-7552
55. Boeckman Jr. R.K., Shao P., and Mulins J. J. Org. Synth. 77 (2000) 141-146