Multicomponent Linchpin Couplings of Silyl Dithianes: Synthesis of the Schreiber C(16-28) Trisacetonide Subtarget for Mycoticins A and B

Organic Letters

Volumn 1, Issue 12, 1999, Pages 2001-2004

  Smith III, Amos B ^a   Pitram, Suresh M ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; MACROLIDE; MYCOTICIN A; MYCOTICIN B;

ARTICLE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ANTI-BACTERIAL AGENTS; MACROLIDES; MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0033576439     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991166b     Document Type: Article

References (30)

1. (a) Omura, S. Macrolide Antibiotics: Chemistry, Biology, Practice; Academic Press: New York, 1984.
2. (b) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021.
3. Structure determination: (a) Maehr, H.; Yang, R.; Hong, L.-N.; Liu, C.-M.; Hatada, M. H.; Todaro, L. J. J. Org. Chem. 1992, 57, 4793.
4. Syntheses: (b) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753.
5. (c) Mori Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299.
6. (d) Mori, Y.; Asai, M.; Kawade, J.; Furukawa, H. Tetrahedron 1995, 57, 5315.
7. Rychnovsky, S. D.; Richardson, T. I.; Rogers, B. N. J. Org. Chem. 1997, 62, 2925.
8. Structure determination: (a) Schreiber, S. L.; Goulet, M. T. Tetrahedron Lett. 1987, 28, 6001.
9. (b) Schreiber, S. L.; Goulet, M. T.; Sammakia, T. Tetrahedron Lett. 1987, 29, 6005.
10. (c) Schreiber, S. L.; Goulet, M. T. J. Am. Chem. Soc. 1987, 109, 8120.
11. Synthesis: (d) Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360.
12. For recent reviews of polyol syntheses: (a) Schneider, C. Angew. Chem. Int. Ed. 1998, 37, 1375.
13. (b) Oishi, T.; Nakata, T. Synthesis 1990, 635.
14. Rychnovsky, S. D.; Khire, U. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058.
15. Richardson, T. I.; Rychnovsky, S. D. J. Am. Chem. Soc. 1997, 119, 12360.
16. Smith, A. B., III; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925.
17. Tietze, L. F.; Geissler, H.; Gewert, J. A.; Jakobi, U. Synlett 1994, 511.
18. (a) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron 1996, 52, 503.
19. (b) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1993, 34, 1951.
20. (a) Smith, A. B., III; Zhuang, L.; Brook, C. S.; Lin, Q.; Moser, W. H.; Trout, R. E. L. Boldi, A. M. Tetrahedron Lett. 1997, 38, 8671.
21. (b) Smith, A. B., III; Lin, Q.; Nakayama, K.; Boldi, A. M.; Brook, C. S.; McBriar, M. D.; Moser, W. H.; Sobukawa, M.; Zhuang, L. Tetrahedron Lett. 1997, 38, 8675.
22. Rychnovsky, S. D.; Griesgraber, G.; Zeller, S.; Skalitzky, D. J. J. Org. Chem. 1991, 56, 5161.
23. 13C NMR. and high-resolution mass spectra.
24. These compounds were prepared via addition of the corresponding silyl dithiane to the requisite epoxide (see ref 8).
25. In our initial studies with the enatiomeric series of compounds, calcium carbonate proved insufficient as a base. The result was removal of the isopropylidene group and formation of the bicyclic compound (+)-ii. (Matrix Presented)
26. Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155.
27. (a) Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945.
28. (b) Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511.
29. (c) Evans, D. A.; Rieger, D. L.; Gage, J. R. Tetrahedron Lett. 1990, 31, 7099.
30. McDougal, P. G.; Rico, J. G.; Oh, Y. I.; Condon, B. D. J. Org. Chem. 1986, 51, 3388.