Natural Product Synthesis via the Rhodium Carbenoid-Mediated Cyclization of α-Diazo Carbonyl Compounds

被引:12
作者
Padwa, Albert [1 ]
Cheng, Bo [1 ]
Zou, Yan [1 ]
机构
[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA
基金
美国国家科学基金会;
关键词
INTRAMOLECULAR DIPOLAR CYCLOADDITIONS; DIELS-ALDER REACTION; CYCLIZATION/CYCLOADDITION CASCADE; ORGANIC-SYNTHESIS; CYCLO-ADDITIONS; TANDEM; MELODINUS; (+/-)-MELOSCINE; ALKALOIDS; CHEMISTRY;
D O I
10.1071/CH13307
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The chemistry of metal carbene complexes has provided chemists with exceptionally fertile ground for designing and developing new stereoselective bond construction for application towards the synthesis of various natural products. In particular, the Rh-II-catalyzed reaction of 2-diazo-3-oxobutanoates bearing tethered pi-bonds represents a synthetically useful protocol for the construction of a variety of novel polycyclic skeletons. The related Rh-II-catalyzed reaction of the 2-diazo-2-(1H-indol-2-yl)acetate system has recently been examined as a potential route towards scandine, a member of the melodinus family of alkaloids.
引用
收藏
页码:343 / 353
页数:11
相关论文
共 101 条
[1]   NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].
BARTON, DHR ;
MCCOMBIE, SW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585
[2]  
BLACK DSC, 1975, SYNTHESIS-STUTTGART, P205
[4]   The synthesis of heterocycles using cascade chemistry [J].
Bur, Scott K. ;
Padwa, Albert .
ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 94, 2007, 94 :1-105
[5]  
Burrell AJM, 2010, CURR ORG SYNTH, V7, P312
[6]  
Carruthers W., 1990, Cycloaddition Reactions In Organic Synthesis, P269
[7]   A tandem metal carbene cyclization-cycloaddition approach to the pseudolaric acids [J].
Chen, B ;
Ko, RYY ;
Yuen, MSM ;
Cheng, KF ;
Chiu, P .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4195-4205
[8]   Cycloaddition Methodology: A Useful Entry Towards Biologically Active Heterocycles [J].
Chiacchio, Ugo ;
Padwa, Albert ;
Romeo, Giovanni .
CURRENT ORGANIC CHEMISTRY, 2009, 13 (05) :422-447
[9]   Application of the carbene cyclization-cycloaddition cascade in total synthesis [J].
Chiu, P .
PURE AND APPLIED CHEMISTRY, 2005, 77 (07) :1183-1189
[10]   A rhodium carbene cyclization-cycloaddition cascade strategy toward the pseudolaric acids [J].
Chiu, P ;
Chen, B ;
Cheng, KF .
ORGANIC LETTERS, 2001, 3 (11) :1721-1724