CONFORMATIONAL STUDIES AND STEREOCHEMICAL ASSIGNMENTS OF THE LACTARANE SESQUITERPENES FUROSCROBICULIN-D AND BLENNIN-D

被引:6
作者
GARLASCHELLI, L
TOMA, L
VIDARI, G
COLOMBO, D
机构
[1] UNIV PAVIA,DIPARTIMENTO CHIM ORGAN,I-27100 PAVIA,ITALY
[2] UNIV MILAN,DIPARTIMENTO CHIM & BIOCHIM MED,I-20133 MILAN,ITALY
关键词
D O I
10.1016/S0040-4020(01)80832-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two lactarane sesquiterpenes, furoscrobiculin D and blennin D, previously isolated from the mushrooms Lactarius scrobiculatus and Lactarius blennius, respectively, have been submitted to conformational analysis by molecular mechanics. The results of the molecular modeling were related to the observed H-1 NMR data and allowed to assign stereostructure 4 to furoscrobiculin D, correcting the previous assignment 1, and stereostructure 5 to blennin D, confirming the previous assignment.
引用
收藏
页码:1211 / 1216
页数:6
相关论文
共 14 条
[1]   FUNGAL METABOLITES .8. STRUCTURES OF NEW SESQUITERPENES FROM LACTARIUS-SCROBICULATUS [J].
BATTAGLIA, R ;
DEBERNARDI, M ;
FRONZA, G ;
MELLERIO, G ;
VIDARI, G ;
VITAFINSI, P .
JOURNAL OF NATURAL PRODUCTS, 1980, 43 (03) :319-328
[2]   BIOGENESIS-LIKE CONVERSION OF MARASMANE TO LACTARANE AND SECO-LACTARANE SKELETON [J].
DEBERNARDI, M ;
VIDARI, G ;
VITAFINZI, P ;
FIASSON, KG .
TETRAHEDRON LETTERS, 1982, 23 (44) :4623-4624
[3]   FUNGAL METABOLITES .20. CHEMICAL CORRELATION OF LACTARANE AND SECOLACTARANE SESQUITERPENES - ABSOLUTE-CONFIGURATION OF FUROSARDONIN-A, LACTARAL AND BLENNIN-C [J].
DEBERNARDI, M ;
FRONZA, G ;
SCILINGO, A ;
VIDARI, G ;
VITAFINZI, P .
TETRAHEDRON, 1986, 42 (15) :4277-4283
[4]   FUNGAL METABOLITES .29. THE CHEMICAL BASIS OF HOT-TASTING AND YELLOWING OF THE MUSHROOMS LACTARIUS-CHRYSORRHEUS AND L-SCROBICULATUS [J].
DEBERNARDI, M ;
GARLASCHELLI, L ;
TOMA, L ;
VIDARI, G ;
VITAFINZI, P .
TETRAHEDRON, 1993, 49 (07) :1489-1504
[5]   FUNGAL METABOLITES .7. STEREOCHEMISTRY OF BLENNIN-A AND BLENNIN-D FROM LACTARIUS-BLENNIUS [J].
DEBERNARDI, M ;
FRONZA, G ;
MELLERIO, G ;
VIDARI, G ;
VITAFINZI, P .
PHYTOCHEMISTRY, 1980, 19 (01) :99-101
[6]  
GAMBAINVERNIZZI A, J NAT PROD 30
[7]   CONFORMATIONS .6. VINYL-ALLYLIC PROTON SPIN COUPLINGS [J].
GARBISCH, EW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (24) :5561-+
[8]   THE RELATIONSHIP BETWEEN PROTON-PROTON NMR COUPLING-CONSTANTS AND SUBSTITUENT ELECTRONEGATIVITIES .1. AN EMPIRICAL GENERALIZATION OF THE KARPLUS EQUATION [J].
HAASNOOT, CAG ;
DELEEUW, FAAM ;
ALTONA, C .
TETRAHEDRON, 1980, 36 (19) :2783-2792
[9]  
PANG Z, 1992, NAT PROD LETT, V1, P65
[10]   THE STRUCTURE OF A NOVEL FUNGAL SESQUITERPENE, ELUCIDATED BY SPECTRAL AND COMPUTATIONAL METHODS [J].
STERNER, O ;
WIK, O ;
CARTER, RE .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1988, 42 (01) :43-47