Further model studies related to fredericamycin A: Analogues in which ring C is expanded to six atoms, and an examination of the diastereoselectivity of radical spirocyclization

Tetrahedron

Volumn 52, Issue 17, 1996, Pages 6085-6116

  Clive, Derrick L J ^a   Kong, Xianglong ^a   Paul, Christine Chua ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

FREDERICAMYCIN A; FREDERICAMYCIN A DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TUMOR CELL;

EID: 0029892113     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00245-1     Document Type: Article

References (24)

1. Clive, D. L. J.; Tao, Y.; Khodabocus, A.; Wu, Y.-J.; Angoh, A. G.; Bennett, S. M.; Boddy, C. N.; Bordeleau, L.; Kellner, D.; Kleiner, G.; Middleton, D. S.; Nichols, C. J.; Richardson, S. R.; Vernon, P. G. J. Amer. Chem. Soc. 1994, 116, 11275.
2. Cf. (a) German Pat. Appl. DE 3430365 A1, 17 Aug. 1984 (Chem. Abstr. 1985, 103, 104798c).
3. (b) See also biological test data reported in this paper.
4. Clive, D. L. J.; Angoh, A. G.; Bennett, S. M. J. Org. Chem. 1987, 52, 1339.
5. (a) Cf. Vedejs, E; Ahmad, S. Tetrahedron Lett. 1988, 29, 2291 and references therein. Huang, W.; Xiao, W.; Wang, J. Youji Huaxue 1986, 376. [Chem. Abstr. 1987, 706, 138113c.]
6. (a) Cf. Vedejs, E; Ahmad, S. Tetrahedron Lett. 1988, 29, 2291 and references therein. Huang, W.; Xiao, W.; Wang, J. Youji Huaxue 1986, 376. [Chem. Abstr. 1987, 706, 138113c.]
7. (a) Cf. Vedejs, E; Ahmad, S. Tetrahedron Lett. 1988, 29, 2291 and references therein. Huang, W.; Xiao, W.; Wang, J. Youji Huaxue 1986, 376. [Chem. Abstr. 1987, 706, 138113c.]
8. (b) Related reagents with the same substitution pattern on phosphorus show poor stereoselectivity with benzaldehyde. This reagent gives E,E-dienes with aliphatic aldehydes; in the one case we had examined (reference 1) it gave an isomer mixture with an aromatic aldehyde. Had it given a single product in the present case, we may have retained the double bonds (see later).
9. Cf. (a) Saint-Jalmes, L.; Lila, C.; Xu, J. Z.; Moreau, L.; Pfeiffer, B.; Eck, G.; Pelsez, L.; Rolando, C.; Julia, M. Bull Chem. Soc. France 1993, 130, 447.
10. (b) Rama Rao, A. V.; Singh, A. K.; Venkateswara Rao, B.; Malla Reddy, K. Tetrahedron Lett. 1993, 34, 2665.
11. Clive, D. L. J.; Khodabocus, A., Vernon, P. G.; Angoh, A. G.; Bordeleau, L.; Middleton, D. S.; Lowe, C.; Kellner, D. J. Chem. Soc., Perkin Trans I 1991, 1433. [Diagram 1 in this reference is incorrectly drawn and should be as diagram 1 here. The methoxy group in Scheme 1 of this reference is also in the wrong position.]
12. Barton, D. H. R.; Kitchin, J. P.; Lester, D. J.; Motherwell, W. B.; Papoula, M. T. B. Tetrahedron Suppl. (No. 1) 1981, 37, 73.
13. Cf. Srikrishna, A.; Reddy, T. J.; Nagaraju, S.; Sattigeri, J. A. Tetrahedron Lett. 1994, 35, 7841. Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S. Tetrahedron Lett. 1994, 35, 429. Srikrishna, A.; Nagaraju, S.; Sharma, G. V. R. J. Chem. Soc., Chem. Commun. 1993, 285. Srikrishna, A.; Viswajanani, R.; Sattigeri, J. A. J. Chem. Soc., Chem. Commun. 1995, 469. Back, T. G; Gladstone, P. L. Synlett 1993, 699.
14. Cf. Srikrishna, A.; Reddy, T. J.; Nagaraju, S.; Sattigeri, J. A. Tetrahedron Lett. 1994, 35, 7841. Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S. Tetrahedron Lett. 1994, 35, 429. Srikrishna, A.; Nagaraju, S.; Sharma, G. V. R. J. Chem. Soc., Chem. Commun. 1993, 285. Srikrishna, A.; Viswajanani, R.; Sattigeri, J. A. J. Chem. Soc., Chem. Commun. 1995, 469. Back, T. G; Gladstone, P. L. Synlett 1993, 699.
15. Cf. Srikrishna, A.; Reddy, T. J.; Nagaraju, S.; Sattigeri, J. A. Tetrahedron Lett. 1994, 35, 7841. Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S. Tetrahedron Lett. 1994, 35, 429. Srikrishna, A.; Nagaraju, S.; Sharma, G. V. R. J. Chem. Soc., Chem. Commun. 1993, 285. Srikrishna, A.; Viswajanani, R.; Sattigeri, J. A. J. Chem. Soc., Chem. Commun. 1995, 469. Back, T. G; Gladstone, P. L. Synlett 1993, 699.
16. Cf. Srikrishna, A.; Reddy, T. J.; Nagaraju, S.; Sattigeri, J. A. Tetrahedron Lett. 1994, 35, 7841. Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S. Tetrahedron Lett. 1994, 35, 429. Srikrishna, A.; Nagaraju, S.; Sharma, G. V. R. J. Chem. Soc., Chem. Commun. 1993, 285. Srikrishna, A.; Viswajanani, R.; Sattigeri, J. A. J. Chem. Soc., Chem. Commun. 1995, 469. Back, T. G; Gladstone, P. L. Synlett 1993, 699.
17. Cf. Srikrishna, A.; Reddy, T. J.; Nagaraju, S.; Sattigeri, J. A. Tetrahedron Lett. 1994, 35, 7841. Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S. Tetrahedron Lett. 1994, 35, 429. Srikrishna, A.; Nagaraju, S.; Sharma, G. V. R. J. Chem. Soc., Chem. Commun. 1993, 285. Srikrishna, A.; Viswajanani, R.; Sattigeri, J. A. J. Chem. Soc., Chem. Commun. 1995, 469. Back, T. G; Gladstone, P. L. Synlett 1993, 699.
18. 2 → RCHO → RH. The last step (RCHO → RH) might, perhaps, be done by decarbonylation or by oxidation and radical decarboxylation.
19. The tests were run at the NCI (Bethesda).
20. Supplied by Chemical Dynamics Corp., South Plainfield, NJ.
21. Phosphomolybdic acid (15 g) and ceric ammonium sulfate (2.5 g) dissolved in a mixture of water (985 mL) and concentrated sulfuric acid (15 mL).
22. Fieser, M.; Fieser, L. F. Reagents for Organic Synthesis; Wiley: New York, 1975; Vol. 5, p 522.
23. Clive, D. L. J.; Daigneault, S. J. Org. Chem. 1991, 56, 3801.
24. Clive, D. L. J.; Sedgeworth, J. J. Heterocycl. Chem. 1987, 24, 509.