Singlet oxygen reactions of 3-methoxy-2-pyrrole carboxylic acid tert-butyl esters. A route to 5-substituted pyrrole precursors of prodigiosin and analogs

Tetrahedron

Volumn 60, Issue 34, 2004, Pages 7419-7425

  Wasserman, Harry H ^a   Xia, Mingde ^a   Wang, Jianji ^a   Petersen, Anders K ^a   Jorgensen, Michael ^a   Power, Patricia ^a   Parr, Jonathan ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

Bipyrrole; Prodigiosin; Pyrrole; Singlet oxygen

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; PRODIGIOSIN; PYRROLE DERIVATIVE; SINGLET OXYGEN;

CONFERENCE PAPER; PRECURSOR; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 3342931241     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.05.053     Document Type: Conference Paper

References (16)

1. Blum H.R. Photodynamic Action and Diseases Caused by Light. 1941;Van Nostrand-Reinhold, New York
2. Wasserman H.H., Power P., Petersen A.K. Tetrahedron Lett. 37:1996;6657-6659. and references cited therein
3. Wasserman H.H., Lipshutz B.H. Wasserman H.H., Murray R.W. Singlet Oxygen. 1979;Academic, New York. Chapter 9
4. Wasserman H.H., Xia M., Wang J., Petersen A.K., Jorgensen M. Tetrahedron Lett. 40:1999;6145-6148
5. Wasserman H.H., Petersen A.K., Xia M., Wang J. Tetrahedron Lett. 40:1999;7587-7589
6. Wasserman H.H., Cook J.D., Fukuyama J.M., Rotello V.M. Tetrahedron Lett. 30:1989;1721-1724
7. 8,9
8. Wasserman H.H., Liberles A. J. Am. Chem. Soc. 82:1960;2086-2088
9. de Mayo P., Reid S.T. Chem. Ind. 1962;1576-1577
10. Prodigiosin, the parent member of this group, shows potent antibacterial and cytotoxic properties although its high toxicity militates against its use as a therapeutic agent. See: Harashima K., Tsuchida N., Tanaka T., Nagasatu J. Agric. Biol. Chem. 31:1967;481-489
11. For a recent review of work on the synthesis of prodigiosin and other natural and unnatural tripyrromethene analogues, see Fürstner A. Angew. Chem., Int. Ed. Engl. 42:2003;3582-3603
12. The McFadyen-Stevens reduction is reliable, although inefficient because of the low (30-40%) yields. Clearly, this step needs further study in order to develop an alternative ester to aldehyde conversion
13. Lange's Handbook of Organic Chemistry; Dean, J. A. Ed.; 13th ed. McGraw-Hill: New York, 1985.
14. 16
15. Rapoport H., Holden K.G. J. Am. Chem. Soc. 84:1962;635-642
16. Wasserman H.H., Lombardo L.J. Tetrahedron Lett. 30:1989;1725-1728