Enantioselective synthesis of a Wieland-Miescher ketone bearing an angular hydroxymethyl group

被引:22
作者
Hanselmann, R [1 ]
Benn, M [1 ]
机构
[1] UNIV CALGARY,DEPT CHEM,CALGARY,AB T2N 1N4,CANADA
基金
加拿大自然科学与工程研究理事会;
关键词
D O I
10.1080/00397919608003699
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enatioselective synthesis of (R)-3,4,8,8a-tetrahydro-8a-allyl-1,6-(2H,7H)-naphthalenedione and the degradation of the angular allyl group to a hydroxymethyl group are reported.
引用
收藏
页码:945 / 961
页数:17
相关论文
共 26 条
[1]  
Agami C., 1988, B SOC CHIM FR MAY, V3, P499
[2]  
BUCHSCHACHER P, 1990, J ORGANIC SYNTHESIS, V7, P368
[3]   REMOTE FUNCTIONALIZATION AND MOLECULAR MODELING - OBSERVATIONS RELEVANT TO THE BARTON AND HYPOIODITE REACTIONS [J].
BURKE, SD ;
SILKS, LA ;
STRICKLAND, SMS .
TETRAHEDRON LETTERS, 1988, 29 (23) :2761-2764
[5]   TOTAL SYNTHESIS OF (+)-PERROTTETIANAL-A [J].
HAGIWARA, H ;
UDA, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (07) :1901-1908
[6]   IMPROVED METHODS FOR THE REDUCTIVE ALKYLATION OF METHOXYBENZOIC ACIDS AND ESTERS - APPLICATIONS TO THE SYNTHESIS OF BICYCLIC KETONES [J].
HAMILTON, RJ ;
MANDER, LN ;
SETHI, SP .
TETRAHEDRON, 1986, 42 (11) :2881-2892
[7]   SYNTHESIS OF SUBSTITUTED CIS-DECALINS AS POTENTIAL INSECT ANTIFEEDANTS [J].
JACKSON, WP ;
LEY, SV .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (05) :1516-1519
[8]   STEREOSELECTIVE SYNTHESIS OF CIS-DECALINS VIA DIELS-ALDER AND DOUBLE MICHAEL ADDITION OF SUBSTITUTED NAZAROV REAGENTS [J].
LAVALLEE, JF ;
SPINO, C ;
RUEL, R ;
HOGAN, KT ;
DESLONGCHAMPS, P .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1992, 70 (05) :1406-1426
[9]   ANGULAR HYDROXYMETHYLATION OF DECALIN SYSTEMS [J].
LEJEUNE, J ;
LALLEMAND, JY .
TETRAHEDRON LETTERS, 1992, 33 (21) :2977-2980
[10]   SYNTHESIS OF POLYOXYGENATED TRANS-DECALINS AS POTENTIAL INSECT ANTIFEEDANTS [J].
LEY, SV ;
NEUHAUS, D ;
SIMPKINS, NS ;
WHITTLE, AJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (09) :2157-2162