ortho-prenylphenol photooxygenation as a straightforward access to ortho-(2-hydroxy-3-methylbut-3-enyl)phenols

被引:11
作者
Helesbeux, JJ [1 ]
Guilet, D [1 ]
Séraphin, D [1 ]
Duval, O [1 ]
Richomme, P [1 ]
Bruneton, J [1 ]
机构
[1] Sci Pharmaceut & Ingn Sante, UFR, SONAS, F-49100 Angers, France
关键词
D O I
10.1016/S0040-4039(00)00657-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Photooxygenation (O-1(2)) Of ortho-prenylphenols followed by a reduction (PPh3) at low temperature (-30 degrees C) yields a mixture of ortho-(2-hydroxy-3-methylbut-3-enyl)phenols and ortho-(3-hydroxy-3-methyl-but-1-enyl)phenols. However, by running the two-step sequence at a higher temperature (15 degrees C), the secondary allylic alcohol could be selectively recovered. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4559 / 4562
页数:4
相关论文
共 13 条
[1]   QUINOL EPOXIDES FROM PARA-CRESOL AND ESTRONE BY PHOTOOXYGENATION AND TITANIUM(IV)-CATALYZED OR VANADIUM(V)-CATALYZED OXYGEN-TRANSFER [J].
ADAM, W ;
LUPON, P .
CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (01) :21-25
[2]   NOVEL PHLOROGLUCINOLS FROM THE PLANT MELICOPE-SESSILIFLORA (RUTACEAE) [J].
CHAN, JA ;
SHULTIS, EA ;
CARR, SA ;
DEBROSSE, CW ;
EGGLESTON, DS ;
FRANCIS, TA ;
HYLAND, LJ ;
JOHNSON, WP ;
KILLMER, LB ;
STAIGER, DB ;
WESTLEY, JW .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (09) :2098-2103
[3]  
Guilet D, 1999, HETEROCYCLES, V51, P67
[4]  
ITO C, 1991, CHEM PHARM BULL, V39, P2509, DOI 10.1248/cpb.39.2509
[5]  
ITO C, 1989, CHEM PHARM BULL, V37, P819
[6]   Prenylated flavonoids from Maclura pomifera [J].
Lee, SJ ;
Wood, AR ;
Maier, CGA ;
Dixon, RA ;
Mabry, TJ .
PHYTOCHEMISTRY, 1998, 49 (08) :2573-2577
[7]   6-acylcoumarins from Mesua racemosa [J].
Morel, C ;
Guilet, D ;
Oger, JM ;
Séraphin, D ;
Sévenet, T ;
Wiart, C ;
Hadi, AHA ;
Richomme, P ;
Bruneton, J .
PHYTOCHEMISTRY, 1999, 50 (07) :1243-1247
[8]  
Morel C, 1999, HETEROCYCLES, V51, P2183
[9]   CLAISEN REARRANGEMENTS .8. SYNTHESIS OF COUMARINS, AVICENNOL, DIPETALINE AND DIPETALOLACTONE [J].
MURRAY, RDH ;
FORBES, IT .
TETRAHEDRON, 1978, 34 (09) :1411-1414
[10]   SYNTHESIS OF THE NATURAL COUMARINS, MURRAOL (CM-C2), TRANS-DEHYDROOSTHOL AND SWIETENOCOUMARIN-G [J].
MURRAY, RDH ;
ZEGHDI, S .
PHYTOCHEMISTRY, 1989, 28 (01) :227-230