Butenolide synthesis by molybdenum-mediated hetero-Pauson-Khand reaction of alkynyl aldehydes

被引:70
作者
Adrio, Javier [1 ]
Carretero, Juan C. [1 ]
机构
[1] Univ Autonoma Madrid, Dept Quim Organ, Fac Ciencias, E-28049 Madrid, Spain
关键词
D O I
10.1021/ja0684186
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The highly reactive complex Mo(CO)(3)(DMF)(3) promotes the CO gas-free cyclocarbonylation of 1,5- and 1,6-alkynyl aldehydes under very mild reaction conditions to provide fused butenolides in good yields. This novel Mo-mediated hetero-Pauson-Khand reaction is very general with regard to the substitution at the alkyne terminus and tether (18 tested cases). Using readily available chiral alkynyl aldehydes, this procedure has been applied to the enantio- and stereoselective synthesis of highly substituted bicyclic butenolides, including an intermediate in natural product synthesis.
引用
收藏
页码:778 / 779
页数:2
相关论文
共 29 条
[1]   Mild and efficient molybdenum-mediated Pauson-Khand-type reaction [J].
Adrio, J ;
Rivero, MR ;
Carretero, JC .
ORGANIC LETTERS, 2005, 7 (03) :431-434
[2]  
Adrio J, 2000, ANGEW CHEM INT EDIT, V39, P2906, DOI 10.1002/1521-3773(20000818)39:16<2906::AID-ANIE2906>3.0.CO
[3]  
2-8
[4]  
[Anonymous], TRANSITION METALS OR
[5]   The synthesis of γ-alkylidenebutenolides [J].
Brückner, R .
CURRENT ORGANIC CHEMISTRY, 2001, 5 (06) :679-718
[6]   Heterocyclic α-alkylidene cyclopentenones obtained via a Pauson-Khand reaction of amino acid derived allenynes.: A scope and limitation study directed toward the preparation of tricyclic pyrrole library [J].
Brummond, KM ;
Curran, DP ;
Mitasev, B ;
Fischer, S .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (05) :1745-1753
[7]   Synthesis of dicyclopenta[a,e]pentalenes via a molybdenum carbonyl mediated tandem allenic Pauson-Khand reaction and the X-ray crystal structure of a planar dicyclopenta[a,e]pentalene [J].
Cao, H ;
Van Ornum, SG ;
Deschamps, J ;
Flippen-Anderson, J ;
Laib, F ;
Cook, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (03) :933-943
[8]   A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].
CARLSEN, PHJ ;
KATSUKI, T ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938
[9]  
CHANTANI N, 1998, J AM CHEM SOC, V120, P5335
[10]   Total synthesis of natural bicyclic lactones (+)-dihydrocanadensolide, (±)-avenociolide, and (±)-isoavenociolide via tungsten-π-allyl complexes [J].
Chen, MJ ;
Narkunan, K ;
Liu, RS .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) :8311-8318