SYNTHESIS OF YUEHCHUKENE ANALOGS, MURRAPANINE AND NORMURRAPANINE UTILIZING THERMAL-REACTION OF BETA-(1-HYDROXYBUTENYL)INDOLES UNDER NEUTRALREACTION CONDITIONS

Authors
SHEU JH CHEN YK CHUNG HF SUNG PJ LIN SF
Citation
Jh. Sheu et al., SYNTHESIS OF YUEHCHUKENE ANALOGS, MURRAPANINE AND NORMURRAPANINE UTILIZING THERMAL-REACTION OF BETA-(1-HYDROXYBUTENYL)INDOLES UNDER NEUTRALREACTION CONDITIONS, Heterocycles, 43(8), 1996, pp. 1751-1758
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
43
Issue
8
Year of publication
1996
Pages
1751 - 1758
Database
ISI
SICI code
0385-5414(1996)43:8<1751:SOYAMA>2.0.ZU;2-A
Abstract
beta-(1-Hydroxybutenyl)indoles, which were prepared in high yields fro m indole-3-carboxaldehyde, could be converted into yuehchukene analogu es(8a, b) murrapanine (9a) and normurrapanine (9b) in one step under t hermal-induced reaction conditions in neutral solution of ethylene gly col and water. beta-(1-Hydroxybutenyl)indoles are supposed to be dehyd rated to 1-(beta-indolyl)-1,3-butadienes which react further to yuehch ukene analogues via a Diels-Alder pathway. Murrapanine and normurrapan ine showed a cytotoxicity toward KB cells.