IMINOPHOSPHORANE-MEDIATED IMIDAZOLE RING FORMATION - A NEW AND GENERAL ENTRY TO APLYSINOPSIN-TYPE ALKALOIDS OF MARINE ORIGIN

Authors
MOLINA P ALMENDROS P FRESNEDA PM
Citation
P. Molina et al., IMINOPHOSPHORANE-MEDIATED IMIDAZOLE RING FORMATION - A NEW AND GENERAL ENTRY TO APLYSINOPSIN-TYPE ALKALOIDS OF MARINE ORIGIN, Tetrahedron, 50(7), 1994, pp. 2241-2254
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
7
Year of publication
1994
Pages
2241 - 2254
Database
ISI
SICI code
0040-4020(1994)50:7<2241:IIRF-A>2.0.ZU;2-4
Abstract
Aza Wittig-type reactions of iminophosphoranes 21, derived from ethyl alpha-azido-beta-(3-indolyl)propenoates and triphenylphosphine, with m ethyl isocyanate, carbon dioxide or carbon disulfide provide the corre sponding heterocumulenes 22, 25 and 28 which undergo cyclization by th e action of nitrogenous reagents completing the assemblage of the fram ework of aplysinopsin. Further deprotection leads to naturally occurri ng aplysinopsin analogues.