Synthesis of a linear α-hydroxymethyl-pentapyrrole derivative and its cyclization to uroporphyrinogens

Tetrahedron Letters

Volumn 41, Issue 16, 2000, Pages 2915-2918

  Okada, Kunisuke ^a   Takakura, Hiroyuki ^a   Nomura, Keishi ^a   Saburi, Kiyoshi ^a  

^a MEIJO UNIVERSITY   (Japan)

Author keywords

Coupling reaction; Linear pentapyrrole derivatives; Rearrangement; Spiro pyrrolenine intermediate

Indexed keywords

PYRROLE DERIVATIVE; UROPORPHYRIN; UROPORPHYRINOGEN;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; DRUG TRANSFORMATION; OXIDATION; REACTION ANALYSIS;

EID: 0034655475     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00293-8     Document Type: Article

References (10)

1. Battersby, A. R.; Leeper, F. J. Chem. Rev. 1990, 90, 1261-1274.
2. Scott, A. I. Acc. Chem. Res. 1990, 23, 308-317.
3. Hawker, C. J.; Marshall, S. W.; Spivey, A. C.; Raithby, P. R.; Leeper, F. J.; Battersby, A. R. J. Chem. Soc., Perkin Trans. 1 1998, 1493-1508.
4. Hawker, C. J.; Spivey, A. C.; Leeper, F. J.; Battersby, A. R. J. Chem. Soc., Perkin Trans. 1 1998, 1509-1517.
5. Hawker, C. J.; Petersen, P. M.; Leeper, F. J.; Battersby, A. R. J. Chem. Soc., Perkin Trans. 1 1998, 1519-1530.
6. Petersen, P. M.; Hawker, C. J.; Stanford, N. P. J.; Leeper, F. J.; Battersby, A. R. J. Chem. Soc., Perkin Trans. 1 1998, 1531-1539.
7. Okada, K.; Saburi, K.; Nomura, K.; Tanino, H. Tetrahedron Lett. 1998, 39, 2365-2366.
8. 2:MeOH=200:1) to give 11 (134.6 mg, 71.9%; corrected yield 97.2%) along with 10 (29.12 mg).
9. 2:MeOH (2:1, 5 ml) under Ar, the combined eluates were concentrated under reduced pressure. The residue was used directly for the next reactions.
10. Takakura, H.; Nomura, K.; Tanino, H.; Okada, K. Tetrahedron Lett. 1999, 40, 2989-2992.