Anti aldol reactions of α-alkoxymethyl ketones: Application to the total synthesis of (+)-restricticin

Tetrahedron Letters

Volumn 37, Issue 45, 1996, Pages 8243-8246

  Paterson, Ian ^a   Nowak, Thorsten ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030569363     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01879-5     Document Type: Article

References (25)

1. 1. (a) Schwartz, R. E.; Dufresne, C.; Flor, J. E.; Kempf, A. J.; Wilson, K. E.; Lam, T.; Onishi, J.; Milligan, J.; Fromtling, R. A.; Abruzzo, G. K.; Jenkins, R.; Glazomitsky, K.; Bills, G.; Zitano, L.; Mochales del Val, S.; Omstead, M. N. J. Antibiot. 1991, 44, 463.
2. (b) Hensens, O. D.; Wichmann, C.; Liesch, J.; VanMiddlesworth, F.; Wilson, K.; Schwartz, R. E. Tetrahedron 1991, 47, 3915.
3. 2. (a) Matsukuma, S.; Ohtsuka, T.; Kotaki, H.; Shirai, H.; Sano, T.; Watanabe, K.; Nakayama, N.; Itezono, Y.; Fujiu, M.; Shimma, N.; Yokose, K.; Okuda, T. J. Antibiot. 1992, 45, 151.
4. (b) Aoki, Y.; Yamazaki, T.; Kondoh, M.; Sudoh, Y.; Nakayama, N.; Sekine, Y.; Shimada, H.; Arisawa, M. J. Antibiot. 1992, 45, 160.
5. 3. (a) O'Sullivan, J.; Phillipson, D. W.; Kirsch, D. R.; Fisher, S. M.; Lai, M. H.; Trejo, W. H. J. Antibiot. 1992, 45, 306.
6. (b) Phillipson, D. W.; O'Sullivan, J.; Johnson, J. H.; Bolgar, M. S.; Kahle, A. D. J. Antibiot. 1992, 45, 313.
7. 4. (a) Tsukuda, T.; Watanabe, M.; Ohtsuka, H.; Fujimoto, Y.; Shimma, M. Bioorg. Med. Chem. Lett. 1994, 4, 733.
8. (b) VanMiddlesworth, F.; Milligan, J.; Bartizal, K.; Dufresne, C.; Onishi, J.; Abruzzo, G.; Patchett, A.; Wilson, K. J. Antibiot. 1996, 49, 329.
9. 5. Jendrzejewski, S.; Ermann, P. Tetrahedron Lett. 1993, 34, 615.
10. 6. Tsukuda, T.; Umeda, I.; Masubuchi, K.; Shirai, M.; Shimma, N. Chem. Pharm. Bull. 1993, 41, 1191.
11. 7. For a synthesis of lanomycin, see: Kang, S. H.; Kim, C. M. Synlett 1996, 515.
12. 8. Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182.
13. 9. (a) Paterson, I.; Goodman, J. M; Isaka, M. Tetrahedron Lett. 1989, 30, 7121.
14. (b) Paterson, I.; Norcross, R. D.; Ward, R. A.; Romea, P.; Lister, M. A. J. Am. Chem. Soc. 1994, 116, 11287.
15. (c) Paterson, I. Pure Appl. Chem. 1992, 64, 1821.
16. 4N requires 400.2487.
17. 11. (a) Levin, J. I.; Turos, E.; Weinreb, S. M. Synth. Comm. 1982, 12, 989.
18. (b) Nahm, S., Weinreb, S. M., Tetrahedron Lett. 1981, 22, 3815.
19. 3P=C(Me)CHO (PhMe, 70 °C, 4 h).
20. 13. (a) Brown, H. C.; Dhar, R. K.; Bakshi, R. K.; Pandiarajan, P. K.; Singaram, B. J. Am. Chem. Soc. 1989, 111, 3441.
21. (b) Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 499.
22. (c) Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 2716.
23. 14. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
24. 15. The oxetane i was obtained as a minor product (10-15%) in this cyclisation step. (equation presented)
25. 16. Dess, D. D.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.