Vinyl group protection in porphyrins and chlorins: Organoselenium derivatives

Tetrahedron Letters

Volumn 38, Issue 6, 1997, Pages 937-940

  Brantley, Sarah E ^a   Gerlach, Benjamin ^a   Olmstead, Marilyn M ^a   Smith, Kevin M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIOCHLORIN; PORPHYRIN DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0031562071     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00002-6     Document Type: Article

References (21)

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2. 2. G. W. Kenner, S. W. McCombie and K. M. Smith, Liebigs Ann. Chem. 1973, 1329.
3. 3. E. D. Sturrock, J. R. Bull, R. E. Kirsch, R. K. Pandey, M. O. Senge and K. M. Smith, J. Chem. Soc., Chem. Commun. 1993, 872.
4. 4. (a) K. M. Smith, G. M. F. Bisset and M. J. Bushell, J. Org. Chem., 1980, 45, 2218.
5. (b) B. Gerlach, S. E. Brantley and K. M. Smith, manuscript in preparation.
6. 5. I. Meunier (UC Davis), unpublished results.
7. 6. A. W. Nichol, J. Chem. Soc. (C) 1970, 903.
8. 7. K. B. Sharpless, M. W. Young and R. F. Lauer, Tetrahedron Lett. 1973, 1979.
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12. 11. A. Gossauer and J. -P. Weller, J. Am. Chem. Soc. 1978, 100, 5928.
13. 12. J. -P. Weller and A. Gossauer, Chem. Ber. 1980, 113, 1603.
14. 13. A. Gossauer, F. Nydegger, E. Benedikt and H. -P. Kost, Helv. Chim. Acta 1989, 72, 518.
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19. 6 trimethyl ester 12 is readily available from chlorophyll-a: see ref. 4, and K. M. Smith, D. A, Goff and D. J. Simpson, J. Am. Chem. Soc. 1985, 107, 4946.
20. -3; absolute structure parameter (Flack) -0.02(7). Tables of atom positions, thermal parameters, and a complete listing of bond distances and angles have been deposited at the Cambridge Crystallographic Data Centre.
21. 20. J. Torpey, D. A. Lee, K. M. Smith and P. R. Ortiz de Montellano, J. Am. Chem. Soc. 1996, 118, 9172.