First Total Syntheses of (.+-.)-Isopiline,(.+-.)-Preocoteine,(.+-.)-Oureguattidine and (.+-.)-3-Methoxynordomesticine and the Biological Activities of (.+-.)-3- …

…, P Udomputtimekakul, T Taechowisan…

Index: Nimgirawath, Surachai; Udomputtimekakul, Phansuang; Taechowisan, Thongchai; Wanbanjob, Asawin; Shen, Yuemao Chemical and Pharmaceutical Bulletin, 2009 , vol. 57, # 4 p. 368 - 376

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Citation Number: 11

Abstract

A convenient and economical synthesis of 4-hydroxy-2, 3-dimethoxybenzaldehyde has been developed. This was used as the starting material for the first total syntheses of (±)- isopiline,(±)-preocoteine,(±)-oureguattidine and (±)-3-methoxynordomesticine in which the key step involved formation of ring C of the aporphines by a radical-initiated cyclisation. Although (±)-3-methoxynordomesticine possesses weak antimicrobial activity, it inhibits ...