First total synthesis of (+)-viroallosecurinine

被引:54
作者
Honda, T [1 ]
Namiki, H [1 ]
Watanabe, M [1 ]
Mizutani, H [1 ]
机构
[1] Hoshi Univ, Fac Pharmaceut Sci, Shinagawa Ku, Tokyo 1428501, Japan
关键词
(+)-viroallosecurinine; ring closing-metathesis; chelation controlled addition; Securinega alkaloid; diastereoselective total synthesis;
D O I
10.1016/j.tetlet.2004.05.031
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first diastereoselective chiral synthesis of (+)-viroallosecurinine, isolated front Securinega virosa as a cytotoxic alkaloid, was achieved by using a chelation-controlled addition of an alkyne moiety to the corresponding ketone, and a ring-metathesis, as key reactions. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5211 / 5213
页数:3
相关论文
共 30 条
[1]  
Armstrong SK, 1998, J CHEM SOC PERK T 1, P371
[2]  
Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012
[3]   Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts [J].
Garber, SB ;
Kingsbury, JS ;
Gray, BL ;
Hoveyda, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8168-8179
[4]  
Grela K, 2002, ANGEW CHEM INT EDIT, V41, P4038, DOI 10.1002/1521-3773(20021104)41:21<4038::AID-ANIE4038>3.0.CO
[5]  
2-0
[6]   Recent advances in olefin metathesis and its application in organic synthesis [J].
Grubbs, RH ;
Chang, S .
TETRAHEDRON, 1998, 54 (18) :4413-4450
[7]   RING-CLOSING METATHESIS AND RELATED PROCESSES IN ORGANIC-SYNTHESIS [J].
GRUBBS, RH ;
MILLER, SJ ;
FU, GC .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (11) :446-452
[8]   General method for the palladium-catalyzed allylation of aliphatic alcohols [J].
Haight, AR ;
Stoner, EJ ;
Peterson, MJ ;
Grover, VK .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (21) :8092-8096
[9]   First diastereoselective chiral synthesis of (-)-securinine [J].
Honda, T ;
Namiki, H ;
Kaneda, K ;
Mizutani, H .
ORGANIC LETTERS, 2004, 6 (01) :87-89
[10]   Ru complexes bearing bidentate carbenes: from innocent curiosity to uniquely effective catalysts for olefin metathesis [J].
Hoveyda, AH ;
Gillingham, DG ;
Van Veldhuizen, JJ ;
Kataoka, O ;
Garber, SB ;
Kingsbury, JS ;
Harrity, JPA .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (01) :8-23