Catalyst-controlled regio- and stereoselective synthesis of diverse 12H-6,12-methanodibenzo[d,g][1,3]dioxocines.
We describe an efficient one-pot regio- and stereoselective method for synthesizing diverse 1-hydroxy-12H-6,12-methanodibenzo[d,g][1,3]dioxocines and 3-hydroxy-12H-6,12-methanodibenzo[d,g][1,3]dioxocines using ethylenediammonium diacetate (EDDA) or p-toluenesulfonic acid (PTSA) catalyzed reactions between various resorcinols and a number of 2-hydroxychalcones. These reactions involve a catalyst-controlled cascade Michael-type reaction/double cyclization process. Importantly, these reactions provide a rapid synthetic route to the production of biologically interesting complex molecules that are generally prepared using multi-step reactions.
School of Chemical Engineering, Yeungnam University, Gyeongsan 712-749, Republic of Korea. yrlee@yu.ac.kr.
Likai
L
Xia
Hongyun
H
Cai
Yong Rok
YR
Lee
D001554:Benzene / Q000138:chemical synthesis* / Q000737:chemistry*; D001688:Biological Products / Q000737:chemistry; D002384:Catalysis; D066244:Proton Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
D001688:Biological Products; D001554:Benzene