Concise construction of the tetracyclic core of lycorine-type alkaloids and the formal synthesis of α-lycorane based on asymmetric bifunctional thiourea-catalyzed cascade reaction

被引：36

作者：

Wang, Yao ^{[1
]}

Luo, Yong-Chun ^{[1
]}

Zhang, Hong-Bo ^{[1
]}

Xu, Peng-Fei ^{[1
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 41期

关键词：

CONJUGATE ADDITION; MICHAEL REACTION; AMARYLLIDACEAE; CYCLIZATION; (+/-)-GAMMA-LYCORANE; MALONATE; OLEFINS;

D O I：

10.1039/c2ob26422f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and stereoselective construction of the tetracyclic core of lycorine-type alkaloids and the formal synthesis of alpha-lycorane has been achieved. The feature of the current method is the employment of a bifunctional thiourea-catalyzed cascade reaction as a powerful tool to construct the skeleton of the natural product, which is a challenging yet very rarely explored strategy. As a result, the tetracyclic core is efficiently synthesized in just three simple operations involving two consecutive cascade reactions.

引用

收藏

页码：8211 / 8215

页数：5

相关论文

共 38 条

[1] Novel bifunctional chiral urea and thiourea derivatives as organocatalysts:: Enantioselective nitro-Michael reaction of malonates and diketones [J].

Andres, Jose M. ;

Manzano, Ruben ;

Pedrosa, Rafael .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (17) :5116-5119

[2] BINDING OF (H-3)NARCICLASINE TO EUKARYOTIC RIBOSOMES - STUDY ON A STRUCTURE-ACTIVITY RELATIONSHIP [J].

BAEZ, A ;

VAZQUEZ, D .

BIOCHIMICA ET BIOPHYSICA ACTA, 1978, 518 (01) :95-103

[3] Electrocyclic ring-opening/π-allyl cation cyclization reaction sequences involving gem-dihalocyclopropanes as substrates:: Application to syntheses of (±)-, (+)-, and (-)-γ-lycorane [J].

Banwell, MG ;

Harvey, JE ;

Hockless, DCR ;

Wu, AW .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) :4241-4250

[4] NARCICLASINE - AN ANTIMITOTIC SUBSTANCE FROM NARCISSUS BULBS [J].

CERIOTTI, G .

NATURE, 1967, 213 (5076) :595-&

[5] Total synthesis of enantiopure (+)-γ-lycorane using highly efficient Pd-catalyzed asymmetric allylic alkylation [J].

Chapsal, BD ;

Ojima, I .

ORGANIC LETTERS, 2006, 8 (07) :1395-1398

[6]

Cossy J, 1999, EUR J ORG CHEM, V1999, P1925

[7] Asymmetric organocatalysis: From infancy to adolescence [J].

Dondoni, Alessandro ;

Massi, Alessandro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) :4638-4660

[8] Asymmetric nitroallylation of arylboronic acids with nitroallyl acetates catalyzed by chiral rhodium complexes and its application in a concise total synthesis of optically pure (+)-γ-lycorane [J].

Dong, L ;

Xu, YJ ;

Cun, LF ;

Cui, X ;

Mi, AQ ;

Jiang, YZ ;

Gong, LZ .

ORGANIC LETTERS, 2005, 7 (19) :4285-4288

[9] Asymmetric organocatalytic domino reactions [J].

Enders, Dieter ;

Grondal, Christoph ;

Huettl, Matthias R. M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1570-1581

[10] Intramolecular bromo-amination of 1,4-cyclohexadiene aminal:: one-pot discrimination of two olefins and concise asymmetric synthesis of (-)- γ-lycorane [J].

Fujioka, H ;

Murai, K ;

Ohba, Y ;

Hirose, H ;

Kita, Y .

CHEMICAL COMMUNICATIONS, 2006, (08) :832-834

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