Enantioselective total synthesis of (+)-gliocladin C

被引:88
作者
Overman, Larry E. [1 ]
Shin, Youseung [1 ]
机构
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
关键词
D O I
10.1021/ol062801y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of gliocladin C, a fungal-derived marine alkaloid containing a rare trioxopiperazine fragment, is reported. This asymmetric synthesis establishes the absolute configuration of this structurally novel natural product.
引用
收藏
页码:339 / 341
页数:3
相关论文
共 21 条
[1]   Asymmetric construction of quaternary carbon stereocenters: High stereoselection in Mukaiyama aldol reactions of 2-siloxyindoles with chiral aldehydes [J].
Adhikari, S ;
Caille, S ;
Hanbauer, M ;
Ngo, VX ;
Overman, LE .
ORGANIC LETTERS, 2005, 7 (13) :2795-2797
[2]  
Anthoni U, 1999, ALKAL CHEM, V13, P163, DOI 10.1016/S0735-8210(99)80025-9
[3]   Synthesis of conformationally constrained amino acid and peptide derivatives [J].
Bailey, PD ;
Bannister, N ;
Bernad, M ;
Blanchard, S ;
Boa, AN .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (24) :3245-3251
[4]   OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].
BAL, BS ;
CHILDERS, WE ;
PINNICK, HW .
TETRAHEDRON, 1981, 37 (11) :2091-2096
[5]   Marine natural products [J].
Blunt, JW ;
Copp, BR ;
Munro, MHG ;
Northcote, PT ;
Prinsep, MR .
NATURAL PRODUCT REPORTS, 2006, 23 (01) :26-78
[6]  
CASNATI G, 1973, GAZZ CHIM ITAL, V103, P141
[7]   Total synthesis of 5-N-acetylardeemin and amauromine:: Practical routes to potential MDR reversal agents [J].
Depew, KM ;
Marsden, SP ;
Zatorska, D ;
Zatorski, A ;
Bornmann, WG ;
Danishefsky, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (51) :11953-11963
[8]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[9]   Nematicidal epipolysulfanyldioxopiperazines from Gliocladium roseum [J].
Dong, JY ;
He, HP ;
Shen, YM ;
Zhang, KQ .
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (10) :1510-1513
[10]   Novel cytotoxic thiodiketopiperazine derivatives from a Tilachlidium sp. [J].
Feng, YJ ;
Blunt, JW ;
Cole, ALJ ;
Munro, MHG .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (12) :2090-2092