Synthesis of cleviolide and the scobinolides

被引:28
作者
Hollingworth, GJ [1 ]
Richecoeur, AME [1 ]
Sweeney, J [1 ]
机构
[1] UNIV BRISTOL,SCH CHEM,BRISTOL BS8 1TS,AVON,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 23期
关键词
D O I
10.1039/p19960002833
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium-catalysed cross-coupling reaction of 4-tributylstannylfuran-2(5H)-one 3 with 1-iodo-4- methylpent-3-en-1-yne 4a gives the natural product cleviolide; from this substance may be prepared both (Z)- and (E)-isomers of scobinolide.
引用
收藏
页码:2833 / 2836
页数:4
相关论文
共 12 条
[1]   IODINE-CATALYZED, POSITIONAL ISOMERIZATION OF OLEFINS - A NEW TOOL FOR PRECISE MEASUREMENT OF THERMODYNAMIC DATA [J].
BENSON, SW ;
BOSE, AN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (10) :1385-&
[2]   NATURALLY-OCCURRING TERPENE DERIVATIVES .367. THE 1ST ACETYLENIC MONOTERPENE AND OTHER CONSTITUENTS FROM SENECIO-CLEVELANDII [J].
BOHLMANN, F ;
ZDERO, C ;
KING, RM ;
ROBINSON, H .
PHYTOCHEMISTRY, 1981, 20 (10) :2425-2427
[3]  
COREY EJ, 1972, TETRAHEDRON LETT, V14, P3769
[4]   INTERMOLECULAR AND INTRAMOLECULAR AZOMETHINE YLIDE [3 + 2] DIPOLAR CYCLO-ADDITIONS FOR THE SYNTHESIS OF HIGHLY FUNCTIONALIZED PYRROLES AND PYRROLIDINES [J].
DESHONG, P ;
KELL, DA ;
SIDLER, DR .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) :2309-2315
[5]  
GADIR SA, 1986, J CHEM RES-S, P102
[6]  
HOLLINGWORTH GJ, 1993, SYNLETT, P463
[7]   PREPARATION AND REACTIONS OF 3-TRIBUTYLSTANNYL- AND 4-TRIBUTYLSTANNYL-2-(5H)-FURANONES - PREPARATION OF ARYL FURANONES [J].
HOLLINGWORTH, GJ ;
SWEENEY, JB .
TETRAHEDRON LETTERS, 1992, 33 (46) :7049-7052
[8]  
Knight D.W., 1994, CONTEMP ORG SYNTH, V1, P287, DOI DOI 10.1021/CR60230A002
[9]   DERIVES PROPARGYLIQUES .1. CARBINOLS, CARBAMATES ET ESTERS PROPYNYLIQUES, ET LEUR ACTIVITE HYPNOTIQUE [J].
LAUGER, P ;
PROST, M ;
CHARLIER, R .
HELVETICA CHIMICA ACTA, 1959, 42 (07) :2379-2393
[10]  
Marshal P.G., 1970, RODDS CHEM CARBON CO, V2, P369