A novel approach for total synthesis of cryptophycins via asymmetric crotylboration protocol

Tetrahedron Letters

Volumn 39, Issue 48, 1998, Pages 8771-8774

  Dhokte, Ulhas P ^a   Khau, Vien V ^a   Hutchison, Darrell R ^a   Martinelli, Michael J ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BORIC ACID; CRYPTOPHYCIN DERIVATIVE; MACROLIDE; NATURAL PRODUCT; PINENE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CYANOBACTERIUM; NOSTOC; PURIFICATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

NOSTOC;

EID: 0032569862     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01994-7     Document Type: Article

References (24)

1. (1) Schwartz, R. E.; Hirsch, C. F.; Sesin, D. F.; Flor, J. E.; Chartrain, M.; Fromtling, R. E.; Harris, G. H.; Salvatore, M. J.; Liesch, J. M.; Yudin, K. J. J. Ind. Microbiol 1990, 5, 113.
2. (2) Subbaraju, G. V.; Golakoti, T.; Patterson, G. M.; Moore, R. E. J. Nat. Prod. 1997, 60, 302.
3. (3) Barrow, R. A.; Hemscheidt, T.; Liang, J.; Paik, S.; Moore, R. E.; Tius, M. A. J. Am. Chem. Soc. 1995, 117, 2479.
4. (4) (a) de Muss, J-M.; Erg, R.; Nguyen, D.; Go, B.; Fortin, S.; Lavallee, J-F. Bioog. Med. Chem. Lett. 1996, 6, 1111.
5. (b) Rej, R.; Nguyen, D.; Go, B.; Fortin, S.; Lavallee, J-F. J. Org. Chem. 1996, 61, 6289.
6. (c) Salamonczyk, G. M.; Han, K.; Guo, Z. -w.; Sih, C. J. J. Org. Chem. 1996, 61, 6893.
7. (d) Ali, S. M.; Georg, G. I. Tetrahedron Lett. 1997, 38, 1703.
8. (e) Leahy, J. W.; Gardinier, K. M. J. Org. Chem. 1997, 62, 7098 and references cited therein.
9. (5) a) Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1989, 54, 1570.
10. b) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 105, 5919.
11. (6) McDougal P.G.; Rico, J. G.; Oh, Y-I.; Condon, B. D. J. Org. Chem. 1986, 51, 3383.
12. (7) Siedlecka, R.; Skarzewski, J.; Mlochowski, J. Tetrahedron Lett. 1990, 31, 2177.
13. (8) Brown, H. C.; Joshi, N. N. J. Org. Chem. 1988, 53, 4059.
14. th American Chemical Society Meeting, Dallas, TX, March 29-April 2, 1998.
15. th American Chemical Society Meeting, Dallas, TX, March 29-April 2, 1998.
16. (10) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
17. (11) Nakata, T.; Fukui, M.; Oishi, T. Tetrahedron Lett. 1988, 29, 2219.
18. (12) Synthesized in two steps from ethyl 2-cyano-2-methylpropionate (Thompson, H. W.; Swistok, J. J. Org. Chem 1981, 46, 4907).
19. (13) Jeffrey, P. D.; McCombie, S. W. J. Org. Chem. 1982, 47, 587.
20. (14) Moher, E.; Martinelli, M. J. unpublished results.
21. (15) Openshaw, H. T.; Whittaker, N. J. Chem. Soc. (C), 1969, 89.
22. (16) (a) Heck, R. F. Org. React. (N.Y.) 1982, 27, 345.
23. (b) Heck, R. F. Acc. Chem. Res. 1979, 12, 146.
24. (17) AH the compounds synthesized provided satisfactory spectral and chemical data.