DIHYDROPYRROMETHENONES BY PD(0)-MEDIATED COUPLING OF IODOPYRROLES ANDACETYLENIC AMIDES - SYNTHESIS OF THE A,B-RING SEGMENT OF PHYTOCHROME

Authors
JACOBI PA GUO JS RAJESWARI S ZHENG WJ
Citation
Pa. Jacobi et al., DIHYDROPYRROMETHENONES BY PD(0)-MEDIATED COUPLING OF IODOPYRROLES ANDACETYLENIC AMIDES - SYNTHESIS OF THE A,B-RING SEGMENT OF PHYTOCHROME, Journal of organic chemistry, 62(9), 1997, pp. 2907-2916
Citations number
53
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
9
Year of publication
1997
Pages
2907 - 2916
Database
ISI
SICI code
0022-3263(1997)62:9<2907:DBPCOI>2.0.ZU;2-Z
Abstract
Dihydropyrromethenone derivative 32b, which constitutes the A,B-ring s egment of phytochrome (6), has been prepared in enantiomerically pure form beginning with acetylenic amide 47b and iodopyrrole 27. The key s teps involved the TBAF-catalyzed 5-exo-dig cyclization of the acetylen ic pyrrole 48b, followed by thia-Mitsunobu inversion of the resulting alcohol derivative 31b.