New analogs of the pyripyropene family of ACAT inhibitors via α-pyrone fragmentation and γ-acylation/cyclization

Chemistry Letters

Volumn , Issue 9, 1997, Pages 935-936

  Obata, Rika ^a   Sunazuka, Toshiaki ^a   Tian, Zhiming ^a   Tomoda, Hiroshi ^a   Harigaya, Yoshihiro ^a   Omura, Satoshi ^a   Smith III, Amos B ^b  

^a KITASATO UNIVERSITY   (Japan)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002715660     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.935     Document Type: Article

References (26)

1. a) F. P. Bell, in "Pharmacological Control of Hyperlipidaemia," ed by R. Fears, J. R. Prous Science Publishers, Barcelona, Spain (1986), p 409.
2. b) J. G. Heider, in "Pharmacological Control of Hyperlipidaemia," ed by R. Fears, J. R. Prous Science Publishers, Barcelona, Spain (1986), p 423.
3. c) D. R. Sliskovic and A. D. White, Trends Pharmacol. Sci., 12, 194 (1991).
4. a) S. Omura, H. Tomoda, Y. K. Kim, and H. Nishida, J. Antibiot., 46, 1168 (1993).
5. b) H. Tomoda, Y.-K. Kim, H. Nishida, R. Masuma, and S. Omura, J. Antibiot., 47, 148 (1994).
6. c) Y.-K. Kim, H. Tomoda, H. Nishida, T. Sunazuka, R. Obata, and S. Omura, J. Antibiot., 47, 154 (1994).
7. d) H. Tomoda, N. Tabata, D.-J. Yang, H. Takayanagi, H. Nishida, and S. Omura, J. Antibiot., 48, 495 (1995).
8. e) H. Tomoda, H. Nishida, Y.-K. Kim, R. Obata, T. Sunazuka, S. Omura, J. Bordner, M. Guadliana, P. G. Dormer, and A. B. Smith, III, J. Am. Chem. Soc., 116, 12097 (1994).
9. For leading references to other ACAT inhibitors, see footnote 7 in reference 3a.
10. a) T. Nagamitsu, T. Sunazuka, R. Obata, H. Tomoda, H. Tanaka, Y. Harigaya, S. Ōmura, and A. B. Smith, III, J. Org. Chem., 60, 8126 (1995).
11. b) A. B. Smith, III, T. Kinsho, T. Sunazuka, and S. Ōmura, Tetrahedron Lett., 37, 6461 (1996).
12. c) For a related synthesis of recemic GERI-BP001 (identical to pyripyropene E), see: K. A. Parker and L. Resnick, J. Org. Chem., 60, 5726 (1995).
13. a) R. Obata, T. Sunazuka, Z. Li, H. Tomoda, and S. Omura, J. Antibiot., 48, 749 (1995).
14. b) R. Obata, T. Sunazuka, H. Tomoda, Y. Harigaya, and S. Omura, Bioorg. Med. Chem. Lett., 5, 2683 (1995).
15. c) R. Obata, T. Sunazuka, Z. Li, Z. Tian, Y. Harigaya, N. Tabata, H. Tomoda, and S. Ōmura, J. Antibiot., 49, 1133 (1996).
16. d) R. Obata, T. Sunazuka, Y. Kato, H. Tomoda, Y. Harigaya, and S. Omura, J. Antibiot., 49, 1149 (1996).
17. S. Ōmura, F. Kuno, T. Sunazuka, K. Shiomi, R. Masuma, and Y. Iwai, J. Antibiot., 48, 745 (1995).
18. H. Tomoda, N. Tabata, Y. Nakata, H. Nishida, T. Kaneko, R. Obata, T. Sunazuka, and S. Ōmura, J. Org. Chem., 61, 882 (1996).
19. 7: 383.2069].
20. This fragmentation process appears to be unique, see: T. L. Ho, "Heterolytic Fragmentation of Organic Molecules," Wiley, New York (1993), p 73.
21. 3Na: 621.3075].
22. We previously observed regioselective γ-alkylation of related substrates: A. B. Smith, III and R. M. Scarborough, Jr., Tetrahedron Lett., 44, 4193 (1978).
23. 3: 672.3208].
24. 10: 584.2496].
25. 2. The other aroyl chlorides were commercially available.
26. The evaluations of biological activity will be described in detail elsewhere.