Highly anti-selective conjugate addition of arylcuprates to a γ-alkoxy-α,β-enoate.: A new method to address stereochemical challenges presented by Amaryllidaceae alkaloids

被引:14
作者
Manpadi, M [1 ]
Kornienko, A [1 ]
机构
[1] New Mexico Inst Min & Technol, Dept Chem, Socorro, NM 87801 USA
关键词
acyclic stereoselection; arylcuprate; amaryllidaceae alkaloids;
D O I
10.1016/j.tetlet.2005.05.006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Various substituted arylcuprates undergo stereocontrolled additions to a D-mannitol-derived gamma-alkoxy-alpha, beta-enoate with exclusive anti-selectivity. The method is well suited for the preparation of a broad range of biologically active Amaryllidaceae alkaloids and their aromatic analogues. A model accounting for the stereochemical outcome of this process is presented. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4433 / 4437
页数:5
相关论文
共 44 条
[1]   CYTOTOXICITY OF HYMENOCALLIS-EXPANSA ALKALOIDS [J].
ANTOUN, MD ;
MENDOZA, NT ;
RIOS, YR ;
PROCTOR, GR ;
WICKRAMARATNE, DBM ;
PEZZUTO, JM ;
KINGHORN, AD .
JOURNAL OF NATURAL PRODUCTS, 1993, 56 (08) :1423-1425
[2]   TOTAL SYNTHESIS OF (+/-)-PANCRATISTATIN [J].
DANISHEFSKY, S ;
LEE, JY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) :4829-4837
[3]   A convergent synthesis of (+)-pancratistatin based on intramolecular electrophilic aromatic substitution [J].
Doyle, TJ ;
Hendrix, M ;
VanDerveer, D ;
Javanmard, S ;
Haseltine, J .
TETRAHEDRON, 1997, 53 (32) :11153-11170
[4]   A short synthesis of (+)-narciclasine via a strategy derived from stereocontrolled epoxide formation and SnCl4-catalyzed arene-epoxide coupling [J].
Elango, S ;
Yan, TH .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :6954-6959
[5]   ANTIVIRAL (RNA) ACTIVITY OF SELECTED AMARYLLIDACEAE ISOQUINOLINE CONSTITUENTS AND SYNTHESIS OF RELATED SUBSTANCES [J].
GABRIELSEN, B ;
MONATH, TP ;
HUGGINS, JW ;
KEFAUVER, DF ;
PETTIT, GR ;
GROSZEK, G ;
HOLLINGSHEAD, M ;
KIRSI, JJ ;
SHANNON, WM ;
SCHUBERT, EM ;
DARE, J ;
UGARKAR, B ;
USSERY, MA ;
PHELAN, MJ .
JOURNAL OF NATURAL PRODUCTS, 1992, 55 (11) :1569-1581
[6]   CHEMICAL-CONSTITUENTS OF AMARYLLIDACEAE .29. ISOCARBOSTYRIL ALKALOIDS FROM HAEMANTHUS-KALBREYERI [J].
GHOSAL, S ;
SINGH, S ;
KUMAR, Y ;
SRIVASTAVA, RS .
PHYTOCHEMISTRY, 1989, 28 (02) :611-613
[7]   A short chemoenzymatic synthesis of (+)-narciclasine [J].
Gonzalez, D ;
Martinot, T ;
Hudlicky, T .
TETRAHEDRON LETTERS, 1999, 40 (16) :3077-3080
[8]   Lipase PS (Pseudomonas cepacia) mediated resolution of γ-substituted γ-((acetyloxy)methyl)-γ-butyrolactones:: Complete stereochemical reversion by substituents [J].
Ha, HJ ;
Yoon, KN ;
Lee, SY ;
Park, YS ;
Lim, MS ;
Yim, YG .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :8062-8066
[9]   Stereocontrolled sequential functionalization in acyclic systems by exploiting internal 1,2-asymmetric induction - Generation of symmetry-related polyamino alcohol motifs [J].
Hanessian, S ;
Wang, WG ;
Gai, YH .
TETRAHEDRON LETTERS, 1996, 37 (42) :7477-7480
[10]  
HANESSIAN S, 1991, SYNTHESIS-STUTTGART, P1083