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■ Synthesis of Yuehchukene Analogues, Murrapanine and Normurrapanine Utylizing Thermal Reaction of β-(1-Hydroxybutenyl)indoles under Neutral Reaction Conditions

Jyh-Horng Sheu,* Yua-Kuang Chen, Huey-Fen Chung, Ping-Jyun Sung, and Song-Fong Lin

*Institute of Marine Resources, National Sun Yat Sen University, 70 Lien-Hai Rd., Kaohsiung, 80424, Taiwan, R.O.C.

Abstract

β-(1-Hydroxybutenyl)indoles, which were prepared in high yields from indole-3-carboxaldehyde, could be converted into yuehchukene analogues (8a,b), murrapanine (9a) and normurrapanine (9b) in one step under thermal-induced reaction conditions in neutral solution of ethylene glycol and water. β-(1-Hydroxybutenyl)indoles are supposed to be dehydrated to 1-(β-indolyl)-1,3-nutadienes which react further to yuehchukene analogues via a Diels-Alder pathway. Murrapanine and normurrapanine showed a cytotoxicity toward KB cells.