Concise Synthesis of (±)-Rhinacanthin A, Dehydro α-Lapachone, and β-Lapachone, and Pyranonaphthoquinone Derivatives

被引：6

作者：

Wang, Xue ^{[1
]}

Chen, Ye ^{[1
]}

Lee, Yong Rok ^{[1
]}

机构：

[1] Yeungnam Univ, Sch Chem Engn & Technol, Gyongsan 712749, South Korea

来源：

BULLETIN OF THE KOREAN CHEMICAL SOCIETY | 2011年 / 32卷 / 01期

基金：

新加坡国家研究基金会;

关键词：

Pyranonaphthoquinones; Rhinacanthin A; Dehydro-alpha-lapachone; beta-Lapachone; PROSTATE-CANCER CELLS; TABEBUIA-AVELLANEDAE; NAPHTHOQUINONES; APOPTOSIS; CONSTITUENTS; INHIBITORS; INDUCTION; RHINACANTHIN; SUPEROXIDE; TARGET;

D O I：

10.5012/bkcs.2011.32.1.153

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise synthesis of (+/-)-rhinacanthin A is achieved in two steps by epoxidation of dehydro-alpha-lapachone, followed by chemo- and regioselective reduction. Dehydro-alpha-lapachone was also synthesized in two steps starting from 4-methoxy-1-naphthol by ethylenediamine diaetate (EDDA)-catalyzed benzopyran formation and a CAN-mediated oxidation reaction. beta-Lapachone was synthesized in three steps from 4-methoxy-1-naphthol by benzopyran formation, catalytic hydrogenation, and Jones oxidation. As additional reactions, synthesis of pyranonaphthoquinone derivatives with the pyranokunthone B skeleton has been achieved in a single step from readily available 2-hydroxy-6-methoxy1,4-naphthoquinone and 2-hydroxy-7-methoxy-1,4-naphthoquinone.

引用

页码：153 / 156

页数：4