Approaches to the synthesis of ingenol

Chemical Society Reviews

Volumn 26, Issue 5, 1997, Pages 387-399

  Kim, Sanghee ^a,b   Winkler, Jeffrey D ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 8544248595     PISSN: 03060012     EISSN: None     Source Type: Journal    
DOI: 10.1039/cs9972600387     Document Type: Article

References (22)

1. H. Opferkuch and E. Hecker, Tetrahedron Lett., 1974, 15, 261.
2. R. R. Upadhyay and G. Mohaddes, Curr. Sci., 1987, 56, (20), 1058.
3. For recent reviews, see P. J. Blackshear, J. Biol. Chem., 1993, 268, 1501; L. V. Decker and P. J. Parker, Trends in Biochem. Sci., 1994, 19, 73.
4. For recent reviews, see P. J. Blackshear, J. Biol. Chem., 1993, 268, 1501; L. V. Decker and P. J. Parker, Trends in Biochem. Sci., 1994, 19, 73.
5. R. Schmidt and A. Aitken, in Naturally Occuring Phorbol Esters, ed. F. Evans, CRC Press, Inc., Boca Raton, 1986, pp. 245; E. Hecker, in Carcinogenesis: A Comprehensive Survey, Mechanisms of Tumor Promotion and Cocarcinogenesis, vol. 2; ed. T. J. Slaga, A. Sivak and R. K. Boutwell, Raven, New York, 1987, p. 11.
6. R. Schmidt and A. Aitken, in Naturally Occuring Phorbol Esters, ed. F. Evans, CRC Press, Inc., Boca Raton, 1986, pp. 245; E. Hecker, in Carcinogenesis: A Comprehensive Survey, Mechanisms of Tumor Promotion and Cocarcinogenesis, vol. 2; ed. T. J. Slaga, A. Sivak and R. K. Boutwell, Raven, New York, 1987, p. 11.
7. J. D. Winkler, B.-C. Hong and S. Kim, Synlett, 1995, 533, and references cited therein.
8. Recently X-ray crystal structure of PKC-phorbol ester complex have been advanced to explain the pharmacophore of the PKC activators, see Chem. Eng. News, 1995, Oct. 23, p. 21; and references cited therein.
9. B. Shearer, B. Sullivan, J. Carter, R. Mathew, P. Waid, J. Connor, R. Patch and R. Buch, J. Med. Chem., 1991, 34, 2931; and for a review of PKC regulation; P. C. Gordge and W. J. Ryves, Cellular Signalling, 1994, 6, 871.
10. B. Shearer, B. Sullivan, J. Carter, R. Mathew, P. Waid, J. Connor, R. Patch and R. Buch, J. Med. Chem., 1991, 34, 2931; and for a review of PKC regulation; P. C. Gordge and W. J. Ryves, Cellular Signalling, 1994, 6, 871.
11. P. Wender and F. McDonald, J. Am. Chem. Soc., 1990, 112, 4956.
12. For recent review of the synthesis of tumour-promoting diterpenes, see: J. H. Rigby, in Studies in Natural Products Chemistry, ed. A.-u. Rahman; Elsevier Science Publishers, Amsterdam, 1993, 12, p. 233.
13. For a recent review of inside-outside chemistry, see: R. W. Alder and S. P. East, Chem. Rev. 1996, 96, 2097.
14. R. Funk, T. A. Olmstead and M. Parvez, J. Am. Chem. Soc., 1988, 110, 3298.
15. J. H. Rigby, S. D. Rege, V. P. Sandanayaka and M. Kirova, J. Org. Chem., 1996, 61, 842.
16. J. H. Rigby and S. V. Cuisiat, J. Org. Chem., 1993, 58, 6286.
17. R. Funk and G. Bolton, J. Am. Chem. Soc., 1986, 108, 4655.
18. M. Harmata, S. Elahmad and C. L. Barnes, Tetrahedron Lett., 1995, 36, 1397.
19. G. Mehta and V. Pathak, J. Chem. Soc., Chem. Commun., 1987, 876.
20. L. Paquette, R. Ross and J. Springer, J. Am. Chem. Soc., 1988, 110, 6192 and references cited therein.
21. R. Funk, T. A. Olmstead, M. Parvez and J. B. Stallman, J. Org. Chem., 1993, 58, 5873.
22. J. H. Rigby, V. S. Claire, S. V. Cuisiat and M. J. Heeg, J. Org. Chem., 1996, 61, 7992.