Enantioselective synthesis of the C10-C20 fragment of fusicoccin A

Journal of Organic Chemistry

Volumn 76, Issue 16, 2011, Pages 6694-6702

  Richter, Anja ^a,b   Hedberg, Christian ^a,b   Waldmann, Herbert ^a,b  

^a TU DORTMUND UNIVERSITY   (Germany)

^b MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC OXIDATION; CYCLOPENTENONES; DIASTEREOSELECTIVE ADDITIONS; DITERPENES; ENANTIOSELECTIVE SYNTHESIS; FULLY PROTECTED; FUNCTIONALIZED; FUSICOCCIN; GRIGNARD; HYDROBORATION; ISOPROPENYL SUBSTITUENTS; TOTAL SYNTHESIS;

OLEFINS;

REACTION INTERMEDIATES;

CYCLOPENTENE DERIVATIVE; CYCLOPENTENONE DERIVATIVE; FUSICOCCIN; FUSICOCCIN A; HALIDE; UNCLASSIFIED DRUG; CYCLOPENTANE DERIVATIVE; CYCLOPENTENONE; DITERPENE; GLYCOSIDE;

ADDITION REACTION; ARTICLE; CATALYSIS; DRUG SYNTHESIS; DRUG TRANSFORMATION; ENANTIOSELECTIVITY; GRIGNARD REACTION; HALOGENATION; HYDROBORATION; OXIDATION; STEREOCHEMISTRY; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CYCLOPENTANES; DITERPENES; GLYCOSIDES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 80051754125     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201020v     Document Type: Article

References (35)

1. Ballio, A.; Mauri, M.; Chain, E.; Deleo, P.; Tonolo, A.; Erlanger, B. Nature 1964, 203, 297
2. Aducci, P.; Marra, M.; Fogoliano, V.; Fullone, M. J. Exp. Bot. 1995, 46, 1463
3. Würtele, M.; Jelich-Ottmann, C.; Wittinghofer, A. EMBO J. 2003, 22, 987
4. Ottmann, C.; Marco, S.; Jaspert, N.; Marcon, C.; Schauer, N.; Weyand, M.; Vandermeeren, C.; Duby, G.; Boutry, M.; Wittinghofer, A.; Rigaud, J.-L.; Oecking, C. Mol. Cell 2007, 25, 427
5. Muslin, A.; Tanner, J.; Allen, P.; Shaw, A. Cell 1996, 84, 889
6. Hermeking, H. Nat. Rev. Cancer 2003, 3, 931
7. Rose, R.; Erdmann, S.; Bovens, S.; Wolf, A.; Rose, M.; Hennig, S.; Waldmann, H.; Ottmann, C. Angew. Chem., Int. Ed. 2010, 49, 4129
8. de Vries-van Leeuwen, I. J.; Kortekaas-Thijssen, C.; Mandouckou, J. A. N.; Kas, S.; Evidente, A.; de Boer, A. H. Cancer Lett. 2010, 293, 198
9. Asahi, K.; Honma, Y.; Hazeki, K.; Sassa, T.; Kubohara, Y.; Sakurai, A.; Takahashi, N. Biochem. Biophys. Res. Commun. 1997, 238, 758
10. Honma, Y.; Ishii, Y.; Sassa, T.; Asahi, K.-I. Leukemia Res. 2003, 27, 1019
11. Kasukabe, T.; Okabe-Kado, J.; Kato, N.; Sassa, T.; Honma, Y. Breast Cancer Res. 2005, 7, 1097
12. Kato, N.; Okamoto, H.; Takeshita, H. Tetrahedron 1996, 52, 3921
13. Li, F.; Kato, N.; Mori, A.; Takeshita, H.; Sassa, T. Chem. Lett. 1997, 12, 1207
14. Kato, N.; Kataoka, H.; Ohnuchi, S.; Tanaka, S.; Takeshita, H. J. Chem. Soc., Chem. Commun. 1988, 5, 354
15. Song, D.; McDonald, R.; West, F. Org. Lett. 2006, 8, 4075
16. Molander, G.; Harris, C. J. Am. Chem. Soc. 1995, 117, 3705
17. Williams, D. R.; Robinson, L. A.; Nevill, C. R.; Reddy, J. P. Angew. Chem., Int. Ed. 2007, 46, 915
18. Paquette, L.; Sun, L.; Friedrich, D.; Savage, P. J. Am. Chem. Soc. 1997, 119, 8438
19. Molander, G.; McKie, J. J. Org. Chem. 1995, 60, 872
20. Molander, G.; McKie, J. J. Org. Chem. 1994, 59, 3186
21. Cram, D.; Elhafez, F. J. Am. Chem. Soc. 1952, 74, 5828
22. Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191
23. Berkessel, A.; Menche, D.; Sklorz, C.; Schröder, M.; Paterson, I. Angew. Chem., Int. Ed. 2003, 42, 1032
24. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392
25. Won, Y.; Joung, U.; Kwon, H.; Lee, B. J. Organomet. Chem. 2003, 677, 133
26. Johnson, C.; Adams, J.; Braun, M.; Senanayake, C.; Wovkulich, P.; Uskokovic, M. Tetrahedron Lett. 1992, 33, 917
27. Bovonsombat, P.; Angam, G.; Edward Mc, N. Tetrahedron Lett. 1994, 35, 6787
28. Janessen, C.; Simons, L.; Godefroi, E. Synthesis 1982, 389
29. Sharples, K.; Lauer, R. J. Am. Chem. Soc. 1972, 94, 7154
30. Pearson, A.; Chen, Y.; Han, G.; Hsu, S.; Ray, T. J. Chem. Soc., Perkin Trans. 1 1985, 267
31. Corey, E.; Helal, C. Angew. Chem., Int. Ed. 1998, 37, 1987
32. Hoye, T. R.; Jeffrey, C. S.; Shao, F. Nat. Protoc. 2007, 2, 2451
33. Stern, A.; Rohde, J.; Swenton, J. J. Org. Chem. 1989, 54, 4413
34. Wang, Q.; Chen, C. Org. Lett. 2008, 10, 1223
35. Brown, H.; Ramachandran, P. J. Organomet. Chem. 1995, 500, 1