Synthesis of a dihydroxylated dienediyne analogue related to neocarzinostatin chromophore

Tetrahedron Letters

Volumn 38, Issue 28, 1997, Pages 5035-5036

  Caddick, Stephen ^a   Khan, Safraz ^a   Smith, Nichola J ^a   Barr, Douglas M ^a   Delisser, Vern M ^a  

^a UNIVERSITY OF SUSSEX   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DIENEDIYNE DERIVATIVE; NATURAL PRODUCT; UNCLASSIFIED DRUG; ZINOSTATIN;

ARTICLE; CANCER INHIBITION; CHROMATOPHORE; DRUG DESIGN; DRUG SYNTHESIS; HYDROXYLATION; IMMERSION; STRUCTURE ACTIVITY RELATION;

EID: 0030879416     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01063-0     Document Type: Article

References (14)

1. Murphy, J. A.; Griffiths, J. Nat. Prod. Rep. 1993, 550. Lhermitte, H.; Grierson, D. S. Cont. Org. Synth. 1996, 3, 41. ibid. 93. Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39, 2103.
2. Murphy, J. A.; Griffiths, J. Nat. Prod. Rep. 1993, 550. Lhermitte, H.; Grierson, D. S. Cont. Org. Synth. 1996, 3, 41. ibid. 93. Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39, 2103.
3. Murphy, J. A.; Griffiths, J. Nat. Prod. Rep. 1993, 550. Lhermitte, H.; Grierson, D. S. Cont. Org. Synth. 1996, 3, 41. ibid. 93. Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39, 2103.
4. Murphy, J. A.; Griffiths, J. Nat. Prod. Rep. 1993, 550. Lhermitte, H.; Grierson, D. S. Cont. Org. Synth. 1996, 3, 41. ibid. 93. Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39, 2103.
5. For lead references to synthetic/analogue studies see Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Magnus, P. Tetrahedron, 1994, 50, 1397. Wender, P. A.; Tebbe, M. J. Tetrahedron, 1994, 50, 1419. Myers, A. G.; Hammond, M.; Wu, Y.; Xiang, J. N.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1996, 118, 10006. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett, 1997, 250.
6. For lead references to synthetic/analogue studies see Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Magnus, P. Tetrahedron, 1994, 50, 1397. Wender, P. A.; Tebbe, M. J. Tetrahedron, 1994, 50, 1419. Myers, A. G.; Hammond, M.; Wu, Y.; Xiang, J. N.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1996, 118, 10006. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett, 1997, 250.
7. For lead references to synthetic/analogue studies see Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Magnus, P. Tetrahedron, 1994, 50, 1397. Wender, P. A.; Tebbe, M. J. Tetrahedron, 1994, 50, 1419. Myers, A. G.; Hammond, M.; Wu, Y.; Xiang, J. N.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1996, 118, 10006. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett, 1997, 250.
8. For lead references to synthetic/analogue studies see Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Magnus, P. Tetrahedron, 1994, 50, 1397. Wender, P. A.; Tebbe, M. J. Tetrahedron, 1994, 50, 1419. Myers, A. G.; Hammond, M.; Wu, Y.; Xiang, J. N.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1996, 118, 10006. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett, 1997, 250.
9. For lead references to synthetic/analogue studies see Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. Magnus, P. Tetrahedron, 1994, 50, 1397. Wender, P. A.; Tebbe, M. J. Tetrahedron, 1994, 50, 1419. Myers, A. G.; Hammond, M.; Wu, Y.; Xiang, J. N.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1996, 118, 10006. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett, 1997, 250.
10. Caddick, S.; Khan, S. J. Chem. Soc. Chem. Commun. 1995, 1971.
11. Caddick, S.; Delisser, V. M. Tetrahedron Lett. 1997, 38, 2355.
12. For a lead reference to innovative early work on monocyclic dienediyne analogues see Wender, P. A.; Tebbe, M. J. Tetrahedron Lett. 1991, 32, 4863.
13. Ratio of isomers obtained was at least 10:1 in favour of the isomer shown in scheme 2.
14. All compounds are racemic, isolated yields are quoted and all compounds exhibited spectroscopic data consistent with their structure.