RESIN ACIDS .15. OXIDATIVE TRANSFORMATIONS OF LEVOPIMARIC ACID-ACETYLENEDICARBOXYLIC ESTER ADDUCT

被引:16
作者
HERZ, W
BLACKSTONE, RC
机构
[1] Department of Chemistry, Florida State University, Tallahassee
关键词
D O I
10.1021/jo01257a015
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The oxidation of certain Diels-Alder adducts of levopimaric acid was investigated with a view to preparing intermediates suitable for the synthesis of polycyclic molecules. Oxidation proceeded satisfactorily only in the presence of a 1a-4a double bond. Because of its accessibility the adduct of levopimaric acid and acetylenedicarboxylic ester was used as model for studying the oxidative transformations of such compounds and was found to undergo a number of unusual reactions. © 1969, American Chemical Society. All rights reserved.
引用
收藏
页码:1257 / +
页数:1
相关论文
共 27 条
[1]   STEREOCHEMISTRY OF MALEOPIMARIC ACID AND LONG RANGE SHIELDING EFFECT OF OLEFINIC BOND [J].
AYER, WA ;
STOTHERS, JB ;
MCDONALD, CE .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1963, 41 (05) :1113-&
[2]   OZONOLYSIS OF CONJUGATED SYSTEMS .1. CLEAVAGE OF STEROIDAL DELTA 1,4-DIEN-3-ONES IN C1903 AND C2105 SERIES [J].
CASPI, E ;
SCHMID, W ;
TAQUIKHA.B .
TETRAHEDRON, 1962, 18 (JUN) :767-&
[3]  
Criegee R, 1942, LIEBIGS ANN CHEM, V550, P99
[4]  
FIESER LF, 1967, REAGENTS ORGANIC SYN, V1, P142
[5]   STRUCTURE + STEREOCHEMISTRY OF DIELS-ALDER ADDUCTS OF LEVOPIMARIC ACID [J].
HALBROOK, NJ ;
HERZ, W ;
LAWRENCE, RV ;
DRESSLER, RL ;
BLACKSTO.RC .
JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (05) :1017-&
[6]   RESIN ACIDS .11. CONFIGURATION AND TRANSFORMATIONS OF LEVOPIMARIC ACID-P-BENZOQUINONE ADDUCT [J].
HERZ, W ;
BLACKSTO.RC ;
NAIR, MG .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (10) :2992-&
[7]   SYNTHESIS OF METHYL 13,16-CYCLOATISAN-18-OATE (METHYL ANTI-TRACHYLOBANATE) [J].
HERZ, W ;
MIRRINGT.RN ;
YOUNG, H ;
LIN, YY .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (11) :4210-&
[8]   RESIN ACIDS .8. REACTIONS OF LEVOPIMARIC ACID WITH ACETYLENIC DIENOPHILES [J].
HERZ, W ;
BLACKSTO.RC ;
NAIR, MG .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (06) :1800-&
[9]  
HERZ W, TO BE PUBLISHED
[10]   DIE PERMANGANATOXYDATION VON 1,5-DIENVERBINDUNGEN [J].
KLEIN, E ;
ROJAHN, W .
TETRAHEDRON, 1965, 21 (09) :2353-&