BORON HALIDE CATALYZED REGIOSELECTIVE ORTHO-CLAISEN REARRANGEMENTS OF 4'-ALLYLOXYCOUMARIC ACID-DERIVATIVES - TOTAL SYNTHESIS OF DEMETHYLSUBEROSIN

被引:16
作者
CAIRNS, N
HARWOOD, LM
ASTLES, DP
ORR, A
机构
[1] UNIV OXFORD,DYSON PERRINS LAB,OXFORD OX1 3QY,ENGLAND
[2] SHELL RES LTD,SITTINGBOURNE RES CTR,SITTINGBOURNE ME9 8AG,KENT,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 21期
关键词
D O I
10.1039/p19940003095
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
6-Allyl-7-hydroxycoumarin 3 and the naturally occurring linear coumarin, demethylsuberosin (7-hydroxy-6-prenylcoumarin) 7 have been prepared in goods yields via regioselective boron halide catalysed ortho-Claisen rearrangements, This procedure provides an efficient alternative approach to linear substituted coumarins without using a halogen to block the 8-(angular) position.
引用
收藏
页码:3095 / 3100
页数:6
相关论文
共 47 条
[21]  
HARWOOD LM, 1986, J CHEM SOC CHEM COMM, P182
[22]  
Heathcote J.G., 1978, AFLATOXINS CHEM BIOL
[23]   NATURE OF PROTHROMBIN BIOSYNTHESIS - PREPROTHROMBINAEMIA IN VITAMIN K-DEFICIENCY [J].
HEMKER, HC ;
HENSEN, A ;
LOELIGER, EA ;
VELTKAMP, JJ .
NATURE, 1963, 200 (490) :589-&
[24]   PROTON MAGNETIC RESONANCE OF SOME COUMARINS AND 2,2-DIMETHYLCHROMENS - FURTHER EXAMPLES OF INTER-RING SPIN-SPIN COUPLING [J].
LASSAK, EV ;
PINHEY, JT .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (20) :2000-&
[25]  
LOUFTY M, 1979, PHARMAZIC, V34, P672
[26]   CATALYSIS OF THE COPE AND CLAISEN REARRANGEMENTS [J].
LUTZ, RP .
CHEMICAL REVIEWS, 1984, 84 (03) :205-247
[27]  
MILLER JA, 1977, BIOL REACT INTERMED, V6, P1975
[28]  
Murray R.D., 1982, NATURAL COUMARINS OC
[29]   CLAISEN REARRANGEMENTS .3. CONVENIENT SYNTHESES OF COUMARINS, OSTHENOL, DEMETHYLSUBEROSIN AND COUMURRAYIN [J].
MURRAY, RDH ;
BALLANTY.MM ;
MATHAI, KP .
TETRAHEDRON, 1971, 27 (06) :1247-&
[30]  
MUSAJO L, 1954, B SOC CHIM BIOL, V36, P1213