An approach to the synthesis of CP-263,114: Complementary routes to the bicyclic ring system via two kinds of fragmentation reaction

Tetrahedron Letters

Volumn 40, Issue 28, 1999, Pages 5215-5218

  Yoshimitsu, Takehiko ^a   Yanagiya, Masahiro ^a   Nagaoka, Hiroto ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Bicyclic aliphatic compounds; Fragmentation reactions; Olefination; Photochemistry

Indexed keywords

FARNESYL TRANS TRANSFERASE; PHOMOIDRIDE B; SQUALENE SYNTHASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG RESEARCH; DRUG SYNTHESIS; PHOTOLYSIS; REDUCTION;

EID: 0033538661     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00941-7     Document Type: Article

References (34)

1. Dabrah TT, Kaneko T, Massefski Jr.W, Whipple EB. J. Am. Chem. Soc. 1997;119:1594-1598.
2. Dabrah TT, Harwood Jr.HJ, Huang LH, Jankovich ND, Kaneko T, Li J-C, Lindsey S, Moshier PM, Subashi TA, Therrien M, Watts PC. J. Antibiot. 1997;50:1-7.
3. Bio MM, Leighton JL. J. Am. Chem. Soc. 1999;121:890-891.
4. Nicolaou KC, Baran PS, Jautelat R, He Y, Fong KC, Choi H-S, Yoon WH, Zhong Y-L. Angew. Chem. Int. Ed. Engl. 1999;38:549-55 2.
5. CHen C, Layton ME, Shair MD. J. Am. Chem. Soc. 1998;120:10784-10785.
6. Waizumi N, Itoh T, Fukuyama T. Tetrahedron Lett. 1998;39:6015-601 8.
7. Kown O, Su D-S, Meng D, Deng W, D'Amico DC, Danishefsky SJ. Angew. Chem. Int. Ed. Engl. 1998;37:1877-1880.
8. Kown O, Su D-S, Meng D, Deng W, D'Amico DC, Danishefsky SJ. Angew. Chem. Int. Ed. Engl. 1998;37:1880-188
9. ARmstrong A, Critchley TJ, Mortlock AA. Synlett 1998;552-553.
10. Sgarbi PWM, Clive DLJ. J. Chem. Soc., Chem. Commun. 1997;2157-215 8.
11. Nicolaou KC, Harter MW, Boulton L, Jandeleit B. Angew. Chem. Int. Ed. Engl. 1997;36:1194-1196.
12. Nicolaou KC, Postema MHD, Miller ND, Yang G. Angew. Chem. Int. Ed. Engl. 1997;36:2821-2823.
13. Davies HML, Calvo R, Ahmed G. Tetrahedron Lett. 1997;38:1737-1740.
14. Zhao R-B, Zhao Y-F, Song G-Q, Wu Y-L. Tetrahedron Lett. 1990;31:3559-3562.
15. Nagaoka H, Shibuya M, Yamada Y. Tetrahedron Lett. 1993;34:1501-1504. and references cited therein.
16. Hegde SG, Wolinsky J. J. Org. Chem. 1982;47:3148-3150.
17. Kito M, Sakai T, Shirahama H, Miyashita M, Matsuda F. Synlett 1997;219-220.
18. Krief A, Laval A-M. Chem Rev. 1999;99:745-777.
19. Molander GA, Harris RH. Chem Rev. 1996;96:307-338.
20. Concepción JI, Francisco CG, Hernández R, Salazar JA, Suárez E. Tetrahedron Lett. 1984;25:1953-1956.
21. Majetich G, Wheless K. Tetrahedron 1995;51:7095-7129.
22. Kalvoda J, Heusler K. Synthesis 1971;501-526.
23. Other types of remote olefination reported so far; Jung ME, Johnson TW. J. Am. Chem. Soc. 1997;119:12412-12413. and references cited therein.
24. Grob CA, Sohiess PW. Angew. Chem. 1967;6:1-14.
25. Other strategies for efficient construction of a bicyclic framework bearing a bridgehead olefin; (a) Kraus GA, Zheng D. Synlett 1993;71-72.
26. (b) Holton RA. J. Am. Chem. Soc. 1984;106:5731-5732.
27. +): 250.1570, found: 250.1572.
28. +): 250.1570, found: 250.1569.
29. Suginome H, Yamada S. Tetrahedron Lett. 1987;28:3963-3966.
30. Saicie RN. Tetrahedron Lett. 1997;38:295-298.
31. Arencibia RN, Salazar JA, Suárez E. Tetrahedron Lett. 1994;35:7463-7466.
32. Lee J, Oh J, Jin S-J, Choi J-R, Atwood JL, Cha JK. J. Org. Chem. 1994;59:6955-6964.
33. Mowbray CE, Pattenden G. Tetrahedron Lett. 1993;34:127-130.
34. Rao AVR, Reddy ER, Joshi BV, Yadav JS. Tetrahedron Lett. 1987;28:6497-6500.