First synthesis of a highly strained cyclodeca-1,5-diyne skeleton via intramolecular Sonogashira cross-coupling

被引:16
作者
Dai, WM [1 ]
Wu, AX [1 ]
机构
[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China
关键词
reactions; diynes; alkenyl halides; cyclization;
D O I
10.1016/S0040-4039(00)01890-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cyclization of alkenyl bromides 6 and 11 containing a terminal alkyne was achieved by using an intramolecular cross-coupling reaction catalyzed by Pd(0) and Cu(I). Under the optimal reaction conditions, cyclodeca-1,5-diyne derivatives 7 and 12 were obtained in 43 and 28% yields, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:81 / 83
页数:3
相关论文
共 27 条
[1]  
[Anonymous], PADDADIUM REAGENTS C
[2]   Synthesis of (+/-)-calicheamicinone by two related methods [J].
Clive, DLJ ;
Bo, YX ;
Tao, Y ;
Daigneault, S ;
Wu, YJ ;
Meignan, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (20) :4904-4905
[3]   THE ESPERAMICIN-CALICHEAMICIN AGLYCONES - RING-CLOSURE OF A SIMPLE STRAINED SYSTEM MEDIATED BY CHROMIUM(II)-NICKEL(II) SALTS [J].
CREVISY, C ;
BEAU, JM .
TETRAHEDRON LETTERS, 1991, 32 (27) :3171-3174
[4]   Synthesis and DNA cleavage study of a 10-membered ring enediyne formed via allylic rearrangement [J].
Dai, WM ;
Fong, KC ;
Lau, CW ;
Zhou, L ;
Hamaguchi, W ;
Nishimoto, S .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :682-683
[5]   Regioselective synthesis of acyclic cis-enediynes via an acid-catalyzed rearrangement of 1,2-dialkynylallyl alcohols.: Syntheses, computational calculations, and mechanism [J].
Dai, WM ;
Wu, JL ;
Fong, KC ;
Lee, MYH ;
Lau, CW .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (14) :5062-5082
[6]   First synthesis of cis-enediynes from 1,5-diynes by an acid-mediated allylic rearrangement [J].
Dai, WM ;
Fong, KC .
TETRAHEDRON LETTERS, 1996, 37 (46) :8413-8416
[7]   Synthesis of cis-enediynes from 1,5-diynes by rearrangement of an allylic double bond [J].
Dai, WM ;
Fong, KC ;
Danjo, H ;
Nishimoto, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (07) :779-781
[8]   Regiocontrolled synthesis of cis-enediynes via intramolecular trapping of allylic cations [J].
Dai, WM ;
Lee, MYH .
TETRAHEDRON LETTERS, 1998, 39 (44) :8149-8152
[9]   Eu(fod)3-catalyzed rearrangement of allylic esters possessing a chelating site.: Application to enediyne synthesis [J].
Dai, WM ;
Lee, MYH .
TETRAHEDRON LETTERS, 1999, 40 (12) :2397-2400
[10]   THE 10-MEMBERED RING ANALOGS OF NEOCARZINOSTATIN CHROMOPHORE - DESIGN, SYNTHESIS, AND MODE OF DECOMPOSITION [J].
HIRAMA, M ;
FUJIWARA, K ;
SHIGEMATU, K ;
FUKAZAWA, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) :4120-4122