Singlet oxygen in synthesis. Formation of d,l- and meso- isochrysohermidin from a 3,3'-bipyrrole precursor

Tetrahedron

Volumn 53, Issue 26, 1997, Pages 8731-8738

  Wasserman, Harry H ^a   Rotello, Vincent M ^a   Frechette, Roger ^a   DeSimone, Robert W ^a   Yoo, Ji Uk ^a   Baldino, Carmen M ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ISOCHRYSOHERMIDIN; OXYGEN; SINGLET OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; DRUG SYNTHESIS; EXTRACTION; OXIDATION; OXYGEN TRANSPORT; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0030818774     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00204-4     Document Type: Article

References (25)

1. Wasserman, H.H.; Cook, J.D.; Fukuyama, J.M.; Rotello, V.M. Tetrahedron Lett. 1989, 30, 1721.
2. Wasserman, H.H.; Lombarde, L.J. Tetrahedron Lett. 1989, 30, 1725.
3. Wasserman, H.H.; Vu, C.B. Tetrahedron Lett. 1994, 35, 9779.
4. a) Masui, Y.; Kawabe, C.; Matsumoto, K.; Abe, K.; Miwa, T. Phytochem. 1986, 25, 1470.
5. b) Abe, K.; Okada, T.; Masui, Y.; Miwa, T. Chemistry Express 1990, 5, 13.
6. c) Abe, K.; Okada, T.; Masui, Y.; Miwa, T. Phytochem. 1989, 28, 960.
7. Lightner, D.A.; Quistad, G.B. J. Heterocycl. Chem. 1973, 10, 273.
8. Lightner, D.A.; Crandall, D.C. Experientia 1973, 29, 262.
9. Bromination of 6 by the procedure of Monrose gave a 1:1 mixture of 3-methoxy-4-bromo pyrrole-2-carboxylate and the corresponding 4,5-dibromo product. Monrose, T.; Tanaka, T.; Yokota, T.; Nagamoto, N.; Yamada, K. Chem. Pharm. Bull. 1978, 26, 3521.
10. Grigg, R.; Johnson, A.W. J. Chem. Soc. 1964, 3315.
11. a) Tiecco, M.; Testaterri, L.; Tingoli, M.; Chianbelli, D.; Montanucci, M. Synthesis 1984, 736.
12. b) Dehmlow, E.; Schulz, H.-J. Liebigs Ann. Chem. 1987, 1123.
13. a) Gjos, N.; Gronowitz, S. Acta Chem. Scand. 1971, 25, 2596.
14. b) Hampton, K.; Christie, J. J. Org. Chem. 1975, 26, 3887.
15. Corey, E.J.; Posner, G. J. Am. Chem. Soc. 1967, 89, 3911.
16. Wasserman, H.H.; Lipshutz, B.H. Chapter IX in Singlet Oxygen, Academic Press Inc. 1979, Wasserman, H.H. and Murray, R., Eds., pp. .
17. Wasserman, H.H.; Frechette, R.; Rotello, V.M.; Schulte, G. Tetrahedron Lett. 1991, 32, 7571.
18. Wasserman, H.H.; Wolff, M.S.; Stiller, K.; Saito, I.; Pickett, J.E. Tetrahedron 1981, 37, 191.
19. Boger, D.L.; Baldino, C.M. J. Am. Chem. Soc. 1993, 115, 11418.
20. Murray, R.W.; Kaplan, M.L. J. Am. Chem. Soc. 1969, 91, 5358.
21. Wasserman, H.H.; DeSimone, R.W.; Boger, D.L.; Baldino, C.M. J. Am. Chem. Soc. 1993, 115, 8457.
22. 1H NMR spectra of both dl, and meso natural products.
23. Murray, R.W.; Kaplan, M.L. J. Am. Chem. Soc. 1968, 90, 4161.
24. Wasserman, H.H.; Yoo, J.U.; DeSimone, R.W., submitted for publication.
25. 1H NMR spectra of the authentic materials with a spectra of the crude reaction mixture.