Asymmetric synthesis of avenaciolide via cascade palladium catalysed cyclisation-carbonylation of bromodienes

被引:32
作者
Aggarwal, VK [1 ]
Davies, PW [1 ]
Schmidt, AT [1 ]
机构
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
关键词
D O I
10.1039/b403183k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An asymmetric synthesis of the secondary metabolite avenaciolide has been achieved utilising a diastereoselective palladium catalysed cyclisation-carbonylation of bromodienes.
引用
收藏
页码:1232 / 1233
页数:2
相关论文
共 24 条
[1]   Palladium catalysed cyclisation-carbonylation of enynes to give cyclic γ,δ-unsaturated acids [J].
Aggarwal, VK ;
Butters, M ;
Davies, PW .
CHEMICAL COMMUNICATIONS, 2003, (09) :1046-1047
[2]   A palladium catalysed cyclisation-carbonylation of bromodienes:: control in carbonylation over facile β-hydride elimination [J].
Aggarwal, VK ;
Davies, PW ;
Moss, WO .
CHEMICAL COMMUNICATIONS, 2002, (09) :972-973
[3]  
Alcázar E, 2000, EUR J ORG CHEM, V2000, P2285, DOI 10.1002/1099-0690(200006)2000:12<2285::AID-EJOC2285>3.0.CO
[4]  
2-8
[5]   Enantioselective addition of 2-methyl-3-butyn-2-ol to aldehydes:: Preparation of 3-hydroxy-1-butynes [J].
Boyall, D ;
López, F ;
Sasaki, H ;
Frantz, D ;
Carreira, EM .
ORGANIC LETTERS, 2000, 2 (26) :4233-4236
[6]   LONG-RANGE SPIN-SPIN COUPLING IN AVENACIOLIDE AND RELATED COMPOUNDS [J].
BROOKES, D ;
STERNHELL, S ;
TIDD, BK ;
TURNER, WB .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1965, 18 (03) :373-+
[7]   AVENACIOLIDE, AN ANTIFUNGAL LACTONE FROM ASPERGILLUS AVENACEUS [J].
BROOKES, D ;
TIDD, BK ;
TURNER, WB .
JOURNAL OF THE CHEMICAL SOCIETY, 1963, (NOV) :5385-&
[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]   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
[10]   Palladium-catalyzed highly diastereoselective cyclic carbopalladation-carbonylative esterification tandem reaction of iododienes and iodoarylalkenes [J].
Copéret, C ;
Negishi, E .
ORGANIC LETTERS, 1999, 1 (01) :165-167