A concise total synthesis of (±)-bakkenolide A by means of an intramolecular Diels-Alder reaction

被引:26
作者
Back, TG [1 ]
Payne, JE [1 ]
机构
[1] Univ Calgary, Dept Chem, Calgary, AB T2N 1N4, Canada
关键词
D O I
10.1021/ol990747y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(+/-)-Bakkenolide A was prepared in five steps from ethyl 4-benzyloxyacetoacetate by sequential alkylations with tiglyl bromide and cis-5-bromo-1,3-pentadiene, followed by an intramolecular Diels-Alder reaction as the key step. The known 7-epibakkenolide A and novel 10-epi- and 7,10-diepibakkenolide A stereoisomers were obtained as minor byproducts.
引用
收藏
页码:663 / 665
页数:3
相关论文
共 29 条
[1]  
ABE N, 1968, TETRAHEDRON LETT, P369
[2]   Synthesis of tricyclic beta-methylene spiro lactones related to bakkenolides by successive radical cyclization high pressure Diels-Alder reactions [J].
Back, TG ;
Gladstone, PL ;
Parvez, M .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3806-3814
[3]  
CARRUTHERS W, 1990, CYCLOADDITIONS REACT, pCH3
[4]  
Ciganek E., 1984, ORG REACT NY, V32, P1, DOI DOI 10.1002/0471264180.OR032.01
[5]   STEREOCHEMICAL ASPECTS OF THE INTRAMOLECULAR DIELS-ALDER REACTION [J].
CRAIG, D .
CHEMICAL SOCIETY REVIEWS, 1987, 16 (02) :187-238
[6]   AN ELECTRON-SPIN RESONANCE STUDY OF PENTADIENYL AND RELATED RADICALS - HOMOLYTIC FISSION OF CYCLOBUT-2-ENYLMETHYL RADICALS [J].
DAVIES, AG ;
GRILLER, D ;
INGOLD, KU ;
LINDSAY, DA ;
WALTON, JC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1981, (04) :633-641
[7]   APPLICATIONS OF [2,3]-SIGMATROPIC REARRANGEMENTS TO NATURAL-PRODUCTS SYNTHESIS - TOTAL SYNTHESIS OF (+/-)-BAKKENOLIDE-A (FUKINANOLIDE) [J].
EVANS, DA ;
SIMS, CL ;
ANDREWS, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (16) :5453-5461
[8]   THE INTRAMOLECULAR DIELS-ALDER REACTION - RECENT ADVANCES AND SYNTHETIC APPLICATIONS [J].
FALLIS, AG .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (02) :183-234
[9]  
FISCHER NH, 1979, PROGR CHEM ORGANIC N, V38, pCH2
[10]   AN APPROACH TO THE BAKKANES - A SHORT, STEREOCONTROLLED TOTAL SYNTHESIS OF (+/-)-BAKKENOLIDE-A [J].
GREENE, AE ;
DEPRES, JP ;
COELHO, F ;
BROCKSOM, TJ .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (20) :3943-3945