Studies towards the synthesis of the zaragozic acids: Synthesis of the bicyclic acetal core of zaragozic acid C.

Tetrahedron Letters

Volumn 38, Issue 24, 1997, Pages 4301-4304

  Paterson, Ian ^a   Feßner, Klaus ^a   Finlay, M Raymond V ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ZARAGOZIC ACID C;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0343765830     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00885-X     Document Type: Article

References (21)

1. (a) Dufresne, C.; Wilson, K. E.; Zink, D.; Smith, J.; Bergstrom, J. D.; Kurtz, M.; Rew, D.; Nallin, M.; Jenkins, R.; Bartizal, K.; Trainor, C.; Bills, G.; Meinz, M.; Huang, L.; Onishi, J.; Milligan, J.; Mojena, M.; Pelaez, F. Tetrahedron 1992, 48, 10221.
2. (b) Santini, C.; Ball, R. G.; Berger, G. D. J. Org. Chem. 1994, 59, 2261, and references cited therein.
3. (a) Dawson, M. J.; Farthing, J. E.; Marshall, P. S.; Middleton, R. F.; O'Neill, M. J.; Shuttleworth, A.; Stylli, C.; Tait, R. M.; Taylor, P. M.; Wildman, H. G.; Buss, A. D.; Langley, D.; Hayes, M. V. J. Antibiot. 1992, 45, 639.
4. (b) Sidebottom, P. J.; Highcock, R. M.; Lane, S. J.; Procopiou, P. A.; Watson, N. S. J. Antibiot. 1992, 45, 648.
5. For a review of synthetic efforts towards the zaragozic acids/squalestatins, see: Nadin, A.; Nicolaou, K. C. Angew. Chem. Int. Ed. Engl. 1996, 35, 1622.
6. For previous total syntheses of zaragozic acids, see: (a) Nicolaou, K. C.; Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J, E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F. Chem. Eur. J. 1995, 1, 467.
7. (b) Carreira, E. M.; Du Bois, J. J. Am Chem. Soc. 1995, 117, 8106.
8. (c) Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111.
9. (d) Stoermer, D.; Caron, S.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9115.
10. (e) Caron, S.; Stoermer, D.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9126.
11. Paterson, I.; Feßner, K.; Finlay, M. R. V.; Jacobs, M. F. Tetrahedron Lett. 1996, 37, 8803.
12. + 793.4499, found 793.4498.
13. Myers, A. G.; Yang, B. H.; Chen, H.; Gleason, J. L. J. Am. Chem. Soc. 1994, 116, 9361.
14. Brown, H. C.; Randad, R. S.; Bhat, K. S.; Zaidlewicz, M.; Racherla, U. S. J. Am. Chem. Soc. 1990, 112, 2389.
15. Fehr, C. Helv. Chem. Acta. 1983, 66, 2512.
16. Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 1287.
17. Trost, B. M.; Arndt, H. C.; Strege, P. E.; Verhoeven, T. R. Tetrahedron Lett. 1976, 17, 3477.
18. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
19. Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136.
20. Several additional products were also formed in this reaction, presumably arising from alternative acetal systems available to the diastereomeric glycol in 3,4-bisepi-19.
21. However, we cannot rule out the possibility that the acetal 19 is formed rapidly from 21 which then rearranges under the reaction conditions to give 15.