Stereoselective synthesis of C1-C9 and C9-C17 fragments of (+)-13-deoxytedanolide

Tetrahedron

Volumn 66, Issue 17, 2010, Pages 3265-3274

  Yadav, J S ^a   Rami Reddy, N ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

(+) 13 Deoxytedanolide; Chiral auxiliary; Cross metathesis; Cytotoxicity; Evans' aldol; Regioselective Sharpless asymmetric dihydroxylation; Yamaguchi macrolactonization

Indexed keywords

13 DEOXYTEDANOLIDE; 3 [5 (BENZYLOXY)PENTANOYL] 4 ISOPROPYL 1,3 OXAZOLAN 2 ONE; 3 [7 [1 (TERTIARY BUTYL) 1,1 DIPHENYLSILYL]OXY 3 HYDROXY 2,6 DIMETHYLHEPTANOYL] 4 ISOPROPYL 1,3 OXAZOLAN 2 ONE; 4 [2 (4 METHOXYPHENYL) 5 METHYL 1,3 DIOXAN 4 YL] 2 METHYL 1 PENTEN 3 OL; 5 (BENZYLOXY) 2 METHYLPENTAN 1 OL; 5 (BENZYLOXY)PENTANOIC ACID; 5 [(4 METHOXYBENZYL)OXY] 2,6 DIMETHYL 7 OCTEN 1 OL; 5 [1 (TERTIARY BUTYL) 1,1 DIPHENYLSILYL]OXY 4 METHYLPENTAN 1 OL; 5,2 [(4 METHOXYBENZYL)OXY] 1,3,5 TRIMETHYL 4 [(1,1,1 TRIISOPROPYLSILYL)OXY] 5 HEXENYL 2,2 DIMETHYL 1,3 DIOXOLANE 4 CARBOXYLIC ACID; 7 [(4 METHOXYBENZYL)OXY] 4,8 DIMETHYL 3 [(1,1,1 TRIETHYLSILYL)OXY] 9 DECEN 1 OL; 7 [1 (TERTIARY BUTYL) 1,1 DIPHENYLSILYL]OXY 3 [(4 METHOXYBENZYL)OXY] 2,6 DIMETHYLHEPTAN 1 OL; [5 (BENZYLOXY) 2 METHYLPENTYL]OXY(TERTIARY BUTYL)DIPHENYLSILANE; ETHYL 3 HYDROXY 7 [(4 METHOXYBENZYL)OXY] 4,8 DIMETHYL 9 DECENOATE; ETHYL 7 [(4 METHOXYBENZYL)OXY] 4,8 DIMETHYL 3 [(1,1,1 TRIETHYLSILYL) OXY] 9 DECENOATE; MACROLIDE; TERTIARY BUTYL 2,3 DIHYDROXY 5 [(4 METHOXYBENZYL)OXY] 4,6,8 TRIMETHYL 7 [(1,1,1 TRIISOPROPYLSILYL)METHYL] 8 NONENOATE; TERTIARY BUTYL 5 2 [(4 METHOXYBENZYL)OXY] 1,3,5 TRIMETHYL 4 [(1,1,1 TRIISOPROPYLSILYL)OXY] 5 HEXENYL 2,2 DIMETHYL 1,3 DIOXOLANE 4 CARBOXYLATE; TERTIARY BUTYL 5 [(4 METHOXYBENZYL)OXY] 4,6,8 TRIMETHYL 7 [(1,1,1 TRIISOPROPYLSILYL)OXY] 2,8 NONADIENOATE; TERTIARY BUTYL[(2) 4 [(4,5) 2 (4 METHOXYPHENYL) 5 METHYL 1,3 DIOXAN 4 YL] 2 METHYLBUTYLOXY]DIPHENYLSILANE; TERTIARY BUTYL[5 [(4 METHOXYBENZYL)OXY] 2,6 DIMETHYL 7 OCTENYLOXY] DIPHENYLSILANE; TRIISOPROPYL[( 1 1 [2 (4 METHOXYPHENYL)5 METHYL 1,3 DIOXAN 4 YL]ETHYL 2 METHYL 2 PROPENYL)OXY]SILANE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; BIRCH REDUCTION; CHIRALITY; DIHYDROXYLATION; DRUG SYNTHESIS; MACROLACTONIZATION; METHYLATION; OLEFINATION; PRIORITY JOURNAL; SILYLATION; STEREOCHEMISTRY;

EID: 77949908775     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.01.023     Document Type: Article

References (55)

1. Schmitz F.J., Gunasekera S.P., Gopichand Y., Hossain B., and Van der Helm D. J. Am. Chem. Soc. 106 (1984) 7251-7252
2. Fusetani N., Sugawara T., and Matsunaga S. J. Org. Chem. 56 (1991) 4971-4974
3. Nishimura S., Matsunaga S., Yoshida M., Hirota H., Yokoyama S., and Fusetani N. Bioorg. Med. Chem. 13 (2005) 449-454
4. Smith III A.B., Adams C.M., Barbosa S.A.L., and Degnan P. J. Am. Chem. Soc. 125 (2003) 350-351
5. Smith III A.B., Adams C.M., Barbosa S.A.L., and Degnan P. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 12042-12047
6. Ehrlich G., Hassfeld J., Eggert U., and Kalesse M. J. Am. Chem. Soc. 128 (2006) 14038-14039
7. Julian L.D., Newcom J.S., and Roush W.R. J. Am. Chem. Soc. 127 (2005) 6186-6187
8. Joshua R.D., Julian L.D., Newcom J.S., and Roush W.R. J. Am. Chem. Soc. 130 (2008) 16407-16416
9. Matsushima T., Horita K., Nakajima N., and Yonemitsu O. Tetrahedron Lett. 37 (1996) 385-388
10. Matsushima T., Mori M., Nakajima N., Maeda H., Uenish J., and Yonemitsu O. Chem. Pharm. Bull. 46 (1998) 1335-1336
11. Liu J.F., Abiko A., Pei Z., Buske D.C., and Masamune S. Tetrahedron Lett. 39 (1998) 1873-1876
12. Taylor R.E., Ciavarri J.P., and Hearn B.R. Tetrahedron Lett. 39 (1998) 9361-9364
13. Rousch W.R., and Lane G.C. Org. Lett. 1 (1999) 95-98
14. Matsushima T., Mori M., Zheng B.Z., Maeda H., Nakajima N., Uenishi J., and Yonemitsu O. Chem. Pharm. Bull. 47 (1999) 308-321
15. Jung M.E., Karama U., and Marquez R. J. Org. Chem. 64 (1999) 663-665
16. Matsushima T., Zheng B.Z., Maeda H., Nakajima B., Uenishi J., and Yonemitsu O. Synlett (1999) 780-782
17. Smith III A.B., and Lodise S.A. Org. Lett. 1 (1999) 1249-1252
18. Zheng B.Z., Maeda H., Mori M., Kusaka S.I., Yonemitsu O., Matsushima T., Nakajima N., and Uenish J. Chem. Pharm. Bull. 47 (1999) 1288-1296
19. Jung M.E., and Marquez R. Tetrahedron Lett. 40 (1999) 3129-3132
20. Matsushima T., Nakajima N., Zheng B.Z., and Yonemitsu O. Chem. Pharm. Bull. 48 (2000) 855-860
21. Zheng B.Z., Yamauchi M., Dei H., Kusaka S.I., Matsui K., and Yonemitsu O. Tetrahedron Lett. 41 (2000) 6441-6445
22. Zheng B.Z., Yamauchi M., Dei H., and Yonemitsu O. Chem. Pharm. Bull. 48 (2000) 1761-1765
23. Jung M.E., Karama U., and Marquez R. Org. Lett. 2 (2000) 1669-1673
24. Jung M.E., and Lee C.P. Org. Lett. 3 (2001) 333-336
25. Loh T.P., and Feng L.C. Tetrahedron Lett. 42 (2001) 6001-6005
26. Loh T.P., and Feng L.C. Tetrahedron Lett. 42 (2001) 3223-3226
27. Matsui K., Zheng B.Z., Kusaka S.I., Kuroda M., Yoshimoto K., Yamada H., and Yonemitsu O. Eur. J. Org. Chem. (2001) 3615-3624
28. Hearn B.R., Ciavarri J.P., and Taylor R.E. Org. Lett. 4 (2002) 2953-2955
29. Iqbal J., Nyavanandi V.K., Nanduri S., Vasudev R., and Naidu A. Tetrahedron Lett. 47 (2006) 6667-6672
30. Yadav J.S., Rao C.S., Chandrashekar S., and Ramarao A.V. Tetrahedron Lett. 36 (1995) 7717-7720
31. Yadav J.S., Rami Reddy N., Harikrishna V., and Reddy B.V.S. Tetrahedron Lett. 50 (2009) 1318-1320
32. Yadav J.S., and Chetia L. Org. Lett. 9 (2007) 4587-4589
33. Yadav J.S., Abraham S., Reddy M.M., Sabitha G., Sankar A.R., and Kunwar A.C. Tetrahedron Lett. 42 (2001) 4713-4716
34. Yadav J.S., Reddy K.B., and Sabitha G. Tetrahedron 64 (2008) 1971-1982
35. Yadav J.S., Sathaiah K., and Srinivas R. Tetrahedron 65 (2009) 3545-3552
36. Yadav J.S., Srinivas R., and Sathaiah K. Tetrahedron Lett. 47 (2006) 1603-1606
37. Yadav J.S., Ravinder K., and Reddy B.V.S. Synlett (2007) 1957-1960
38. Grubbs R.H. Tetrahedron 60 (2004) 7117-7140
39. Inanaga J., Hirata K., Saeki H., Katsuki T., and Yamaguchi M. Bull. Chem. Soc. Jpn. 52 (1979) 1989-1993
40. Wolf S., Esperanza H.M., and Agosta C.W. J. Org. Chem. 47 (1982) 4358-4359
41. Ruda K., Lindberg J., Garegg P.J., Oscarson S., and Konradsson P. Tetrahedron 56 (2000) 3969-3975
42. Takano S., Akiyama M., Sato S., and Ogasawara K. Chem. Lett. (1983) 1593-1596
43. Mancuso A.J., Huang S.L., and Swern D. J. Org. Chem. 43 (1978) 2480-2482
44. Tomooda K., Kikuchi M., Igawa K., Suzuki M., Keong P.H., and Nakai T. Angew. Chem., Int. Ed. 39 (2000) 4502-4505
45. Harris C.R., Kuduk S.D., Balog A., Savin K., Glunz P.W., and Danishefsky S.J. J. Am. Chem. Soc. 121 (1999) 7050-7062
46. Sharpless K.B., Amberg W., Bennani Y.L., Crispino G.A., Hartung J., Jeong K.S., Kwong H.L., Morikawa K., Wang Z.M., Xu D., and Zhang X.L. J. Org. Chem. 57 (1992) 2768-2771
47. Kolb H.C., VanNieuwenhze M.S., and Sharpless K.B. Chem. Rev. 94 (1994) 2483-2547
48. Tomohiro M., Michiko M., Bao-Zhong Z., Hiroshi M., Noriyuki N., Jun-ichi U., and Osamu Y. Chem. Pharm. Bull. 47 (1999) 308-321
49. Dalcanale E., and Montanari F. J. Org. Chem. 51 (1986) 567-569
50. Guerlavais V., Carroll P.J., and Joullie M.M. Tetrahedron: Asymmetry 13 (2002) 675-680
51. Evans D.A., Bartroli J., and Shih T.L. J. Am. Chem. Soc. 103 (1981) 2127-2129
52. Evans D.A., Vogel E., and Nelson J.V. J. Am. Chem. Soc. 101 (1979) 6120-6123
53. Rama Rao A.V., Chakraborty T.K., and Purandare A.V. Tetrahedron Lett. 31 (1990) 1443-1446
54. Meng D., Bertinato P., Balog A., Su D.-S., Kamenecka T., Sorensen E.J., and Danishefsky S.J. J. Am. Chem. Soc. 119 (1997) 10073-10092
55. Santaniello E., and Manzocchi A. Synthesis (1977) 698-699