SYNTHESIS OF C-17-FUNCTIONALIZED BEYERANE DITERPENES - SYNTHESIS OF (-)-ERYTHROXYLOL-B, (-)-ERYTHROXYDIOL-A AND (-)-BENUOL

被引:30
作者
ABAD, A
AGULLO, C
ARNO, M
MARIN, ML
ZARAGOZA, RJ
机构
[1] Departamento de Química Orgánica, Universitat de Valencia, 46100-Burjasot, Valencia
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 20期
关键词
D O I
10.1039/p19940002987
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title compounds 1, 2 and 3 became accessible from an appropriately functionalized podocarpenone 4 in short sequences of operations, in which the key step involves the; toluene-p-sulfonic acid-induced rearrangement of 13-epimeric epoxides 6 and 7.
引用
收藏
页码:2987 / 2991
页数:5
相关论文
共 22 条
[1]   SYNTHESIS OF (-)-AURICULARIC ACID AND ITS C-4 EPIMER - THE ABSOLUTE-CONFIGURATION OF AURICULARIC ACID [J].
ABAD, A ;
ARNO, M ;
PEIRO, M ;
ZARAGOZA, RJ .
TETRAHEDRON, 1991, 47 (23) :3829-3844
[2]   SPONGIAN PENTACYCLIC DITERPENES - STEREOSELECTIVE SYNTHESIS OF APLYROSEOL-1, APLYROSEOL-2 AND DEACETYLAPLYROSEOL-2 [J].
ABAD, A ;
ARNO, M ;
MARIN, ML ;
ZARAGOZA, RJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (16) :1861-1867
[3]  
ABAD A, 1992, J ORG CHEM, V27, P6861
[4]   ABSOLUTE-CONFIGURATIONS OF 3 ENT-BEYERENE DERIVATIVES [J].
ABBOUD, KA ;
SIMONSEN, SH ;
LEE, EF ;
MABRY, TJ .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1991, 47 :782-787
[5]   MECHANISM OF THE REARRANGEMENT OF THE BICYCLO[4.2.3]OCTAN SYSTEM TO THE BICYCLO[3.2.1]OCTAN SYSTEM [J].
BASTARD, J ;
KHAC, DD ;
FETIZON, M ;
PREVOST, C ;
BELOEIL, JC .
TETRAHEDRON, 1991, 47 (02) :229-238
[6]   THE 7-NORBORNADIENYL CATION - AN NMR/IGLO VALIDATION OF ITS AB-INITIO STRUCTURE [J].
BREMER, M ;
SCHOTZ, K ;
SCHLEYER, PV ;
FLEISCHER, U ;
SCHINDLER, M ;
KUTZELNIGG, W ;
KOCH, W ;
PULAY, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (08) :1042-1044
[8]  
CONNOLLY JD, 1991, DICT TERPENOIDS, V1, P956
[9]   4 NEW DITERPENES FROM SIDERITIS-SERRAT-A .17. [J].
DEQUESADA, TG ;
RODRIGUEZ, B ;
VALVERDE, S .
PHYTOCHEMISTRY, 1975, 14 (02) :517-519
[10]  
FUJIMOTO Y, 1976, TETRAHEDRON LETT, P3325