The total synthesis of scytophycin C. Part 2: Synthesis of scytophycin C from the protected seco acid

Tetrahedron

Volumn 54, Issue 39, 1998, Pages 11955-11970

  Paterson, Ian ^a   Watson, Christine ^a   Yeung, Kap Sun ^a   Ward, Richard A ^a   Wallace, Paul A ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE;

ARTICLE; CHEMICAL REACTION; ISOMERISM; OXIDATION; POLYMERIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032564015     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)83051-2     Document Type: Article

References (26)

1. Paterson, I.; Yeung, K.-S.; Watson, C.; Ward, R. A.; Wallace, P. A. Tetrahedron 1998, 54, 11935.
2. For a preliminary account of some of this work, see: Paterson, I.; Watson, C.; Yeung, K.-S.; Wallace, P. A.; Ward, R. A. J. Org. Chem. 1997, 62, 452.
3. (a) Paterson, I.; Smith, J. D.; Ward, R. A.; Gumming, J. G. J. Am. Chem. Soc. 1994, 116, 2615.
4. (b) Paterson, I.; Yeung, K.-S.; Ward, R. A.; Smith, J. D.; Cumming, J. G., Lamboley, S. Tetrahedron, 1995, 51, 9467.
5. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
6. Ishibashi, M.; Moore, R. E.; Patterson, G. M. L.; Xu, C.; Clardy, J. J. Org. Chem., 1986, 51, 5300.
7. McMurray, J. Org. React. 1976, 24, 187.
8. (a) Laganis, E. D.; Chenard, B. L. Tetrahedron Lett. 1984, 25, 5831.
9. (b) Bhagwat, S. S.; Hamann, P. R.; Still, W. C. J. Am. Chem. Soc. 1985, 107, 6372.
10. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
11. (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
12. (c) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
13. (d) Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549.
14. For a selective deprotection in a similar situation, see: Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001.
15. Hikota, M.; Sakurai, Y.; Horita, K.; Yonemitsu, O. Tetrahedron Lett. 1990, 31, 6367.
16. Boden, E. P.; Keck, G. E. J. Org. Chem. 1985, 50, 2394.
17. Mukaiyama, T.; Usui, M.; Saigo, K. Chem. Lett. 1976, 49.
18. (a) For a review of transesterification reactions, see: Otera, J. Chem. Rev. 1993, 93, 1449.
19. (b) Seebach, D.; Hungerbühler, E.; Naef, R.; Schnurrenberger, P.; Weidmann, B.; Züger, M. Synthesis 1982, 138.
20. (a) Kigoshi, H.; Suenaga, K.; Mutou, T.; Ishigaki, T.; Atsumi, T.; Ishiwata, H.; Sakakura, A.; Ogawa, T.; Ojika, M.; Yamada, K. J. Org. Chem. 1996, 61, 5326.
21. (b) Ojika, M.; Kigoshi, H.; Ishigaki, T.; Tsukada, I.; Tsuboi, T.; Ogawa, T.; Yamada, K. J. Am. Chem. Soc. 1994, 116, 7441.
22. (c) Kigoshi, H.; Ojika, M.; Ishigaki, T.; Suenaga, K.; Mutou, T.; Sakakura, A.; Ogawa, T.; Yamada, K. J. Am. Chem. Soc. 1994, 116, 7443.
23. Otera, J.; Dan-oh, N.; Nozaki, H. J. Org. Chem. 1991, 56, 5307.
24. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 7, 639.
25. Paterson, I.; Cowden, C.; Watson, C. Synlett 1996, 209.
26. Unfortunately, an authentic sample of scytophycin C was not available from the Hawaii group (Dr G. M. L. Patterson) for direct comparison.