A Palladium-Catalyzed Vinylcyclopropane (3+2) Cycloaddition Approach to the Melodinus Alkaloids

被引:107
作者
Goldberg, Alexander F. G. [1 ]
Stoltz, Brian M. [1 ]
机构
[1] CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA
基金
加拿大自然科学与工程研究理事会;
关键词
CRYSTAL-STRUCTURE; SCANDENS FORST; (+/-)-EPIMELOSCINE; (+/-)-MELOSCINE; (&)-SCANDINE; MELOSCINE;
D O I
10.1021/ol2017615
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed (3 + 2) cycloaddition of a vinylcyclopropane and a beta-nitrostyrene is employed to rapidly assemble the cyclopentane core of the Melodinus alkaloids. The ABCD ring system of the natural product family is prepared In six steps from commercially available materials.
引用
收藏
页码:4474 / 4476
页数:3
相关论文
共 19 条
[1]   AN APOCYNACEAE-ALKALOID OF A NOVEL TYPE [J].
BERNAUER, K ;
ENGLERT, G ;
VETTER, W .
EXPERIENTIA, 1965, 21 (07) :374-&
[2]   STRUCTURE OF MELODINUS ALKALOIDS, (+)-MELOSCINE,(+)-EPIMELOSCINE AND (+)-SCANDINE .1. ALKALOIDS FROM MELODINUS SCANDENS FORST [J].
BERNAUER, K ;
ENGLERT, G ;
VETTER, W ;
WEISS, E .
HELVETICA CHIMICA ACTA, 1969, 52 (07) :1886-&
[3]   CRYSTAL-STRUCTURE AND ABSOLUTE-CONFIGURATION OF (+)-SCANDINE HYDROBROMIDE [J].
CANNON, JR ;
CROFT, KD ;
MATSUKI, Y ;
PATRICK, VA ;
TOIA, RF ;
WHITE, AH .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (08) :1655-1664
[4]   C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF NATURALLY OCCURRING SUBSTANCES .48. DIMERIC QUINOLINIC MELODINUS ALKALOIDS [J].
DAUDON, M ;
MEHRI, MH ;
PLAT, MM ;
HAGAMAN, EW ;
WENKERT, E .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (20) :3275-3278
[5]   A tandem, nitroalkene conjugate addition/[3+2] cycloaddition approach to the synthesis of the pentacyclic core of (±)-scandine [J].
Denmark, Scott E. ;
Cottell, Jeromy J. .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2397-2402
[6]   ALKALOIDS FROM MELODINUS-HEMSLEYANUS [J].
GUO, LW ;
ZHOU, YL .
PHYTOCHEMISTRY, 1993, 34 (02) :563-566
[7]   Total Synthesis of (±)-Meloscine [J].
Hayashi, Yujiro ;
Inagaki, Fuyuhiko ;
Mukai, Chisato .
ORGANIC LETTERS, 2011, 13 (07) :1778-1780
[8]   METHYLENEINDOLINES, INDOLENINES, AND INDOLENINIUMS .20. THE 1ST BIOMIMETIC SYNTHESIS OF SCANDINE AND MELOSCINE [J].
HUGEL, G ;
LEVY, J .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (09) :1594-1595
[9]   SYNTHESIS APPLICATIONS OF CATIONIC AZA-COPE REARRANGEMENTS .20. TOTAL SYNTHESIS OF (+/-)-MELOSCINE AND (+/-)-EPIMELOSCINE [J].
OVERMAN, LE ;
ROBERTSON, GM ;
ROBICHAUD, AJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) :1236-1238
[10]   USE OF AZA-COPE REARRANGEMENT MANNICH CYCLIZATION REACTIONS TO ACHIEVE A GENERAL ENTRY TO MELODINUS AND ASPIDOSPERMA ALKALOIDS - STEREOCONTROLLED TOTAL SYNTHESES OF (+/-)-DEOXOAPODINE, (+/-)-MELOSCINE, AND (+/-)-EPIMELOSCINE AND A FORMAL SYNTHESIS OF (+/-)-1-ACETYLASPIDOALBIDINE [J].
OVERMAN, LE ;
ROBERTSON, GM ;
ROBICHAUD, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (07) :2598-2610