Practical First Total Synthesis of the Potent Phytotoxic (±)-Naphthotectone, Isolated from Tectona grandis

被引：14
作者：
Guerrero-Vasquez, Guillermo A. [1 ]
Andrade, Carlos Kleber Z. [2 ]
Molinillo, Jose M. G. [1 ]
Macias, Francisco A. [1 ]
机构：
[1] Univ Cadiz, Sch Sci, Dept Organ Chem, INBIO Inst Biomol,Allelopathy Grp, Puerto Real 11510, Spain
[2] Univ Brasilia, Inst Quim, Lab Quim Metodol & Organ Sintet LaQMOS, BR-70910970 Brasilia, DF, Brazil
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 27期
关键词：
Total synthesis; Natural products; Napthoquinones; Electrochemistry; Epoxidation; Green chemistry; EMPLOYING STABILIZED YLIDES; NAPHTHOQUINONE DERIVATIVES; CONVENIENT SYNTHESIS; DIMETHYLSULFONIUM METHYLIDE; OXIDATIVE DEMETHYLATION; AMMONIUM-NITRATE; WITTIG REACTIONS; SHIKONIN; CHEMISTRY; QUINONES;
D O I：
10.1002/ejoc.201300783
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Naphthotectone is a quinone isolated recently from teak extracts of Tectona grandis. It has been shown to be one of the most abundant compounds and the most active compound isolated form teak. Thus, it has been proposed that naphthotectone is one of the compounds responsible for the allelophathic activity of this plant. An efficient total synthesis of (+/-)-naphthotectone was achieved in seven steps and 31% overall yield. The best results were obtained by using an aqueous Wittig reaction as a key step. Other reactions used were the formation of an epoxide ring by the Corey-Chaykovsky method, and an innovative one-pot anodic electrooxidation and demethylation.
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页码：6175 / 6180
页数：6
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