Total synthesis of the multidrug-resistance reversing agent hapalosin

Synlett

Volumn , Issue 7, 1999, Pages 1118-1120

  Haddad, Mansour ^a   Botuha, Candice ^a   Larchevêque, Marc ^a  

^a PSL RESEARCH UNIVERSITY   (France)

Author keywords

Epoxyamine; Macrolactamisation; Multidrug resistance; Styrene oxide

Indexed keywords

CYCLODEPSIPEPTIDE; EPOXIDE; ESTER; HAPALOSIN; HYDROXYAMINO ACID; LITHIUM DERIVATIVE; STYRENE OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CONFORMATION; DRUG SYNTHESIS; MULTIDRUG RESISTANCE; OXIDATION; REVERSAL REACTION; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION;

EID: 0032799974     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2765     Document Type: Article

References (24)

1. For reviews, see : (a) Simon, S.M.; Schindler, M. Proc. Natl. Acad. Sci. USA 1994, 91, 3497.
2. (b) Kavallaris, M. Anti-Cancer Drugs 1997, 8, 17.
3. (c) Robert, J. Drugs of the Future 1997, 22, 149.
4. Stratmann, K.; Burgoyne, D.L.; Moore, R.E.; Patterson, G.M.L.; Smith, C.D. J. Org. Chem. 1994, 59, 7219.
5. (a) Dinh, T.Q.; Du X.; Armstrong, R.W. J. Org. Chem. 1996, 61, 6606.
6. (b) Okuno, T.; Ohmori, K.; Nishiyama, S.; Yamamura, S.; Nakamura, K.; Houk, K.N.; Okamoto, K. Tetrahedron 1996, 52, 14723.
7. (a) Dinh, Q.; Armstrong, R.W. J. Org. Chem. 1995, 60, 8118.
8. (b) Ghosh, A.K.; Liu, W.; Xu, Y.; Chen, Z. Angew. Chem. Int. Ed. Engl. 1996, 35, 74.
9. (c) Ohmori, K.; Okuno, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1996, 37, 3467.
10. (d) Wagner, B.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1996, 37, 6557.
11. For the synthesis of analogs, see: Dinh, T.Q.; Smith, C.D.; Armstrong, R.W. J. Org. Chem. 1997, 62, 790; Dinh, T.Q.; Du, X.; Smith, C.D.; Armstrong, R.W. J. Org. Chem. 1997, 62, 6713; Dinh, T.Q.; Smith, C.D.; Du, X.; Armstrong, R.W. J. Med. Chem. 1998, 41, 981.
12. For the synthesis of analogs, see: Dinh, T.Q.; Smith, C.D.; Armstrong, R.W. J. Org. Chem. 1997, 62, 790; Dinh, T.Q.; Du, X.; Smith, C.D.; Armstrong, R.W. J. Org. Chem. 1997, 62, 6713; Dinh, T.Q.; Smith, C.D.; Du, X.; Armstrong, R.W. J. Med. Chem. 1998, 41, 981.
13. For the synthesis of analogs, see: Dinh, T.Q.; Smith, C.D.; Armstrong, R.W. J. Org. Chem. 1997, 62, 790; Dinh, T.Q.; Du, X.; Smith, C.D.; Armstrong, R.W. J. Org. Chem. 1997, 62, 6713; Dinh, T.Q.; Smith, C.D.; Du, X.; Armstrong, R.W. J. Med. Chem. 1998, 41, 981.
14. Pégorier, L.; Petit, Y.; Larchevêque, M. J. Chem. Soc., Chem. Commun. 1994, 633.
15. Pégorier, L.; Petit, Y.; Mambu, A.; Larchevêque, M. Synthesis 1994, 1403.
16. Carlsen, P.J.; Katsuki, T.; Martin, V.; Sharpless, B.K. J. Org. Chem. 1981, 46, 3936.
17. Yamamoto, Y.; Maruyama, K. J. Am. Chem. Soc. 1985, 107, 6411.
18. Botuha, C.; Haddad, M.; Larchevêque, M. Tetrahedron : Asymmetry 1998, 9, 1929.
19. The enantiomeric purity of the alcohol 13 was checked by HPLC using a ChiralPak AD (Daicel) with hexane-iPrOH (99/ 1) and was found better than 98%.
20. Seebach, D.; Hungerbühler, E.; Naef, R.; Schnurrenberger, P.; Weidmann, B.; Züger, M. Synthesis 1982, 138.
21. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
22. 3 in DMF according a procedure described in rei 3b for the allyl ester (Yield:80%).
23. 3) δppm -3.9, 12.8, 13.1, 14.0, 17.1, 18.7, 22.5, 25.3, 25.9, 28.1, 29.0, 29.3, 29.9, 31.7, 34.5, 39.9, 42.8, 43.2, 65.5, 70.1, 70.3, 74.5, 76.7, 79.0, 79.6, 118.6, 125.9, 126.0, 128.0, 128.3, 128.9, 131.5, 139.1, 155.3, 155.7, 168.8, 170.8, 173.3. MS (EI) m/z 570 (M-191, 43), 352 M-409, 44), 207 M-554, 100).
24. +, 10), 398 (100), 298 (9), 267 (27), 217 (19), 167 91).