STEREOSPECIFIC REARRANGEMENTS IN TRICYCLOPENTANOID SESQUITERPENES - THE ABSOLUTE-CONFIGURATION OF (-)-ISOCOMENE, (-)-BETA-ISOCOMENE, AND (-)-SILPHINENE

被引:22
作者
FITJER, L
MONZOOLTRA, H
机构
[1] Institut für Organische Chemie, Universität Göttingen, D-37077 Göttingen
关键词
D O I
10.1021/jo00075a004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The determination of the absolute configuration of (-)-isocomene ((-)-9), (-)-beta-isocomene ((-)-3), and (-)-silphinene ((-)-15) by correlation with (-)-modhephene ((-)-(3aR,4R,6aS)-4) via stereospecific rearrangements is described.
引用
收藏
页码:6171 / 6173
页数:3
相关论文
共 70 条
[1]   NATURALLY OCCURRING DERIVATIVES .108. ANOMAL SESQUITERPENE FROM BERKHEYA-RADULA (HARV) DE WILLD [J].
BOHLMANN, F ;
LEVAN, N ;
PICKARDT, J .
CHEMISCHE BERICHTE-RECUEIL, 1977, 110 (12) :3777-3781
[2]   NATURALLY-OCCURRING TERPENE DERIVATIVES .350. ERIOLANOLIDES, EUDESMANOLIDES AND A REARRANGED SESQUITERPENE FROM ERIOPHYLLUM SPECIES [J].
BOHLMANN, F ;
ZDERO, C ;
JAKUPOVIC, J ;
ROBINSON, H ;
KING, RM .
PHYTOCHEMISTRY, 1981, 20 (09) :2239-2244
[3]   NATURAL TERPENE DERIVATIVES .238. NEW SESQUITERPENE HYDROCARBONS WITH ANOMALOUS CARBON SKELETONS FROM SILPHIUM SPECIES [J].
BOHLMANN, F ;
JAKUPOVIC, J .
PHYTOCHEMISTRY, 1980, 19 (02) :259-265
[4]   NATURALLY OCCURRING TERPENE DERIVATIVES .226. BETA-ISOCOMENE, NEW SESQUITERPENE FROM BERKHEYA SPECIES [J].
BOHLMANN, F ;
LEVAN, N ;
VANCUONGPHAM, T ;
JACUPOVIC, J ;
SCHUSTER, A ;
ZABEL, V ;
WATSON, WH .
PHYTOCHEMISTRY, 1979, 18 (11) :1831-1834
[5]   RADICAL CLEAVAGE OF CYCLOBUTANES - ALTERNATIVE ROUTES TO (+/-)-SILPHINENE [J].
CRIMMINS, MT ;
MASCARELLA, SW .
TETRAHEDRON LETTERS, 1987, 28 (43) :5063-5066
[6]   INTRAMOLECULAR PHOTOCYCLOADDITION CYCLOBUTANE FRAGMENTATION - TOTAL SYNTHESIS OF (+/-)-SILPHINENE [J].
CRIMMINS, MT ;
MASCARELLA, SW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (12) :3435-3438
[7]   THE TANDEM RADICAL CYCLIZATION APPROACH TO ANGULAR TRIQUINANES - MODEL STUDIES AND THE TOTAL SYNTHESIS OF (+/-)-SILPHIPERFOLENE AND (+/-)-9-EPISILPHIPERFOLENE [J].
CURRAN, DP ;
KUO, SC .
TETRAHEDRON, 1987, 43 (23) :5653-5661
[8]   TANDEM RADICAL CYCLIZATION APPROACH TO ANGULAR TRIQUINANES - A SHORT SYNTHESIS OF (+/-)-SILPHIPERFOL-6-ENE AND (+/-)-9-EPISILPHIPERFOL-6-ENE [J].
CURRAN, DP ;
KUO, SC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (05) :1106-1107
[9]   TANDEM TRANSANNULAR RADICAL CYCLIZATIONS - TOTAL SYNTHESES OF (+/-)-MODHEPHENE AND (+/-)-EPI-MODHEPHENE [J].
CURRAN, DP ;
WANG, S .
TETRAHEDRON, 1993, 49 (04) :755-770
[10]   FORMAL TOTAL SYNTHESIS OF (+1-)-ISOCOMENE [J].
DAUBEN, WG ;
WALKER, DM .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (06) :1103-1108