Total synthesis of 15-deoxoclerocidin

Tetrahedron Letters

Volumn 41, Issue 6, 2000, Pages 843-846

  Kende, A S ^a   Rustenhoven, J J ^b   Zimmermann, K ^c  

^a UNIVERSITY OF ROCHESTER   (United States)

^b PHARMACOPEIA INC   (United States)

^c BRISTOL MYERS SQUIBB   (United States)

Author keywords

12 O formyl 15,20 tetrahydroclerocidin; 15 deoxoclerocidin; 15 dihydro 12 O formylclerocidin; Clerocidin; Synthesis

Indexed keywords

12 O FORMYL 15,20 TETRAHYDROCLEROCIDIN; 15 DEOXOCLEROCIDIN; 15 DIHYDRO 12 O FORMYLCLEROCIDIN; CLERODANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

EID: 0034606943     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02206-6     Document Type: Article

References (17)

1. (a) Anderson, N. R.; Lorck, H. O. B.; Rasmussen, P. R. J. Antibiot. 1983, 36, 753-759;
2. (b) Anderson, N. R.; Rasmussen, P. R. Tetrahedron Lett. 1984, 25, 465-468;
3. (c) Anderson, N. R.; Rasmussen, P. R. Tetrahedron Lett. 1984, 25, 469-472.
4. (a) Kawada, S.-z.; Yamashita, Y.; Fujii, N.; Nakano, H. Cancer Res. 1991, 51, 2922-2925;
5. (b) Binaschi, M.; Zagotto, G.; Palumbo, M.; Zunino, F.; Farinosi, R.; Capranico, G. Cancer Res. 1997, 57, 1710-1716.
6. (a) Xiang, A. X.; Watson, D. A.; Ling, T.; Theodorakis, E. A. J. Org. Chem. 1998, 63, 6774-6775.
7. For other syntheses of advanced intermediates, see: (b) Almstead, J.-I. K.; Demuth, T. P.; Ledoussal, B. Tetrahedron: Asymmetry 1998, 9, 3179-3183; (c) Marko, I. E.; Wiaux, M.; Warriner, S. M.; Giles, P. R.; Eustace, P.; Dean, D.; Bailey, M. Tetrahedron Lett. 1999, 40, 5629-5632.
8. For other syntheses of advanced intermediates, see: (b) Almstead, J.-I. K.; Demuth, T. P.; Ledoussal, B. Tetrahedron: Asymmetry 1998, 9, 3179-3183; (c) Marko, I. E.; Wiaux, M.; Warriner, S. M.; Giles, P. R.; Eustace, P.; Dean, D.; Bailey, M. Tetrahedron Lett. 1999, 40, 5629-5632.
9. Jacquet, J. P.; Bouzard, D.; Remuzon P. Tetrahedron Lett. 1993, 34, 823-826.
10. Hagiwara, H.; Uda, H. J. Org. Chem. 1988, 53, 2308.
11. (a) Sarma, A. S.; Chattopadhyay, P. J. Org. Chem. 1982, 47, 1727;
12. (b) Sarma, A. S.; Gayen, A. K. J. Indian Chem. Soc. 1985, 24B, 1208.
13. Baillargeon, V. P.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 452.
14. Oxidation of crude aldol products was necessary to suppress retro-aldol fragmentation.
15. Barrett, A. G. M.; Kamimura, T. J. Chem. Soc., Chem. Commun. 1995, 1756.
16. Bailey, M.; Marko, I. E.; Ollis, W. D.; Rasmussen, P. R. Tetrahedron Lett. 1990, 31, 4509-4512.
17. Prepared from 2-TBDPSilyloxy-N-methyl-N-methoxy-acetamide, analogous to Nemoto, H.; Shiraki, M.; Fukumoto, K. Tetrahedron 1994, 50, 10391.