Total Synthesis of Phenanthro-Quinolizidine Alkaloids: (±)-Cryptopleurine, (±)-Boehmeriasin A, (±)-Boehmeriasin B and (±)-Hydroxycryptopleurine

被引：33

作者：

Cui, Mingbo ^{[1
]}

Wang, Qingmin ^{[1
]}

机构：

[1] Nankai Univ, State Key Lab Elementoorgan Chem, Res Inst Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 31期

基金：

中国国家自然科学基金;

关键词：

Alkaloids; Total synthesis; Structure elucidation; Natural products; Nitrogen heterocycles; DON FAMILY URTICACEAE; PHENANTHROQUINOLIZIDINE ALKALOIDS; BOEHMERIA-CYLINDRICA; SODIUM-BOROHYDRIDE; PHENANTHROINDOLIZIDINE ALKALOIDS; TRIFLUOROACETIC-ACID; TYLOPHORA ALKALOIDS; CYTOTOXIC AGENT; CRYPTOPLEURINE; REDUCTION;

D O I：

10.1002/ejoc.200900834

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesis of (+/-)-boehmeriasin A and B and a concise synthesis of (+/-)-cryptopleurine and (+/-)-hydroxycryptopleurine are described. The piperidine ring of these alkaloids was constructed by the coupling of the phenanthrene ring with 2-bromopyridine through a nucleophilic substitution reaction and subsequent reduction of the resulting pyridyl ketone. The first crystal structure of a phenanthro-quinolizidine alkaloid is also reported. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：5445 / 5451

页数：7

共 52 条

[1] Convenient, benign and scalable synthesis of 2-and 4-substituted benzylpiperidines [J].