Pyrrole-singlet oxygen reactions leading to alpha,alpha '-bipyrroles. Synthesis of prodigiosin and analogs

Authors
Wasserman, HH Petersen, AK Xia, MD Wang, JJ
Citation
Hh. Wasserman et al., Pyrrole-singlet oxygen reactions leading to alpha,alpha '-bipyrroles. Synthesis of prodigiosin and analogs, TETRAHEDR L, 40(43), 1999, pp. 7587-7589
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
43
Year of publication
1999
Pages
7587 - 7589
Database
ISI
SICI code
0040-4039(19991022)40:43<7587:PORLTA>2.0.ZU;2-Z
Abstract
Reaction of the tert-butyl ester of 3-methoxy-2-pyrrolecarboxylic acid with singlet oxygen yields a hydroperoxide intermediate which undergoes couplin g with pyrroles to yield precursors of prodigiosin and ring A analogs, read ily convertible to the corresponding tripyrromethenes. (C) 1999 Elsevier Sc ience Ltd. All rights reserved.