Chemistry of renieramycins. Part 9: Stereocontrolled total synthesis of (±)-renieramycin G

Tetrahedron Letters

Volumn 52, Issue 19, 2011, Pages 2446-2449

  Yokoya, Masashi ^a   Shinada Fujino, Kimiko ^a   Saito, Naoki ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Cytotoxicity; Natural marine product; Renieramycin; Total synthesis

Indexed keywords

BENZALDEHYDE DERIVATIVE; LACTAM; RENIERAMYCIN G; RENIERAMYCIN H; SAFRAMYCIN B; TETRAHYDROISOQUINOLINE; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG ISOLATION; DRUG SYNTHESIS; ISOMERIZATION; STEREOISOMERISM;

EID: 79953677772     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.02.055     Document Type: Article

References (41)

1. Part 8: K. Charupant, N. Daikuhara, E. Saito, S. Amnuoypol, K. Suwanborirux, T. Owa, and N. Saito Bioorg. Med. Chem. 17 2009 4548 4558
2. K.L. Rinehart Med. Drug Rev. 102 2000 1669 1730
3. G.J. Aune, T. Furuta, and Y. Pommier Anticancer Drugs 13 2002 545 555
4. J.D. Scott, and R.M. Williams Chem. Rev. 102 2002 1669 1730
5. Structures of renieramycins A-D (1a-d): J.M. Frincke, and D.J. Faulkner J. Am. Chem. Soc. 104 1982 265 269 errata: 1982, 104, 5004
6. Structures of renieramycins E (1e) and F (1f): H.-Y. He, and D.J. Faulkner J. Org. Chem. 54 1989 5822 5824
7. Structure of renieramycin G (1g): B.S. Davidson Tetrahedron Lett. 33 1992 3721 3724
8. 9 and I (1i): P.S. Parameswaran, C.G. Naik, S.Y. Kamat, and B.N. Pramanik Indian J. Chem., Sect B 37 1998 1258 1263
9. The revised structure of 1h is the same as that of cribrostatin 4: N. Saito, H. Sakai, K. Suwanborirux, S. Pummangura, and A. Kubo Heterocycles 55 2001 21 28
10. Structure of cribrostatin 4: G.R. Pettit, J.C. Knight, J.C. Collins, D.L. Herald, R.K. Pettit, M.R. Boyd, and V.G. Young J. Nat. Prod. 63 2000 793 798
11. Structure of jorumycin: A. Fontana, P. Cavaliere, S. Wahidulla, C.G. Naik, and G. Cimino Tetrahedron 56 2000 7305 7308
12. Structures of jorunnamycins A-C: K. Charupant, K. Suwanborirux, S. Amnuoypol, E. Saito, A. Kubo, and N. Saito Chem. Pharm. Bull. 55 2007 81 86
13. A few SAR studies on renieramycins were reported by using some synthetic derivatives: J.W. Lane, A. Estevez, K. Mortara, O. Callan, J.R. Spencer, and R.M. Williams Bioorg. Med. Chem. Lett. 16 2006 3180 3183
14. B.J.D. Wright, C. Chan, and S.J. Danishefsky J. Nat. Prod. 71 2008 409 414
15. K. Suwanborirux, S. Amnuoypol, A. Plubrukarn, S. Pummangura, A. Kubo, C. Tanaka, and N. Saito J. Nat. Prod. 66 2003 1441 1446
16. S. Amnuoypol, K. Suwanborirux, S. Pummangura, A. Kubo, C. Tanaka, and N. Saito J. Nat. Prod. 67 2004 1023 1028
17. N. Saito, C. Tanaka, Y. Koizumi, K. Suwanborirux, S. Amnuoypol, S. Pummangura, and A. Kubo Tetrahedron 60 2004 3873 3881
18. P. Magnus, and K.S. Matthews J. Am. Chem. Soc. 127 2005 12476 12477
19. J.W. Lane, Y. Chen, and R.M. Williams J. Am. Chem. Soc. 127 2005 12684 12690
20. Y. -C. Wu, and J. Zhu Org. Lett. 11 2009 5558 5561
21. X.W. Liao, W. Liu, W.F. Dong, B.H. Guan, S.Z. Chen, and Z.Z. Liu Tetrahedron 65 2009 5709 5715
22. C. Chan, R. Heid, S. Zheng, J. Guo, B. Zhou, T. Furuuchi, and S.J. Danishefsky J. Am. Chem. Soc. 127 2005 4596 4598
23. G. Vincent, and R.M. Williams Angew. Chem., Int. Ed. 46 2007 1517 1520
24. X. Chen, and J. Zhu Angew. Chem., Int. Ed. 46 2007 3962 3965
25. A. Kubo, N. Saito, H. Yamato, K. Masubuchi, and M. Nakamura J. Org. Chem. 53 1988 4295 4310
26. N. Saito, S. Harada, I. Inouye, K. Yamaguchi, and A. Kubo Tetrahedron 51 1995 8231 8246
27. N. Saito, R. Yamauchi, and A. Kubo Heterocycles 32 1991 1203 1214
28. Our starting material for the E-ring portion of 1g was the commercially available 3,4-dimethoxyphenol, the phenolic OH protection of which followed by three steps (a) n-BuLi, MeI, THF, 0 °C; (b) HCl/EtOH; (c) hexamethylenetetramine (HMPT), AcOH gave 3 in 66% overall yield.
29. A. Kubo, N. Saito, H. Yamato, and Y. Kawakami Chem. Pharm. Bull. 35 1987 2525 2532
30. 2, 0 °C).
31. N. Saito, R. Yamauchi, H. Nishioka, S. Ida, and A. Kubo J. Org. Chem. 54 1989 5391 5395
32. i.
33. The NMR spectrum of 11 displayed H-1 proton as a singlet at δ 4.95 and C-1 carbon at δ 48.0.
34. Y.-A. Chang, T.-H. Sun, M.Y. Chiang, F.-J. Lu, Y.-T. Huang, L.-C. Liang, and C.W. Ong Tetrahedron 63 2007 8781 8787
35. C.W. Ong, V.A. Chang, J.-Y. Wu, and C.-C. Cheng Tetrahedron 59 2003 8245 8249
36. C.W. Ong, and H.C. Lee Aust. J. Chem. 43 1990 773 775
37. N. Saito, R. Seki, N. Kameyama, R. Sugimoto, and A. Kubo Chem. Pharm. Bull. 51 2003 821 831
38. M. Yokoya, O. Kawachi, and N. Saito Heterocycles 76 2008 1497 1509
39. 1 = 0.075 for I > 2.0σ(I)data.
40. For previous data See Figure 3: N. Saito, S. Harada, M. Yamashita, T. Saito, K. Yamaguchi, and A. Kubo Tetrahedron 51 1995 8213 8230
41. -1.