SCALEMIC 12-HYDROXYAMBLIOFURAN AND 12-ACETOXYAMBLIOFURAN, 5 TETRACYCLIC FURANODITERPENES AND A FURANOSESTERTERPENE FROM SPONGIA SP

被引:39
作者
SEARLE, PA [1 ]
MOLINSKI, TF [1 ]
机构
[1] UNIV CALIF DAVIS,DEPT CHEM,DAVIS,CA 95616
关键词
D O I
10.1016/S0040-4020(01)89605-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Eight new compounds were isolated from a Western Australian sponge Spongia sp., including 12-hydroxyambliofuran (5), its acetate ester 6, five new tetracyclic diterpenes 7 - 11 and the epoxyfuranosesterterpene carboxylic acid 12. Compounds 5 and 6, each isolated as a 3:1 mixture of enantiomers as determined by a modified Mosher's ester method and chiral lanthanide NMR shift studies, are rare examples of scalemic marine natural products.
引用
收藏
页码:9893 / 9908
页数:16
相关论文
共 20 条
[1]   CHEMISTRY OF SPONGES .4. SPONGIAN DITERPENES FROM HYATELLA-INTESTINALIS [J].
CAMBIE, RC ;
CRAW, PA ;
STONE, MJ ;
BERGQUIST, PR .
JOURNAL OF NATURAL PRODUCTS, 1988, 51 (02) :293-297
[2]  
CAPELLE N, 1980, B SOC CHIM BELG, V89, P399
[3]   C-13 CHEMICAL-SHIFTS OF SOME MODEL OLEFINS [J].
COUPERUS, PA ;
CLAGUE, ADH ;
VANDONGEN, JPCM .
ORGANIC MAGNETIC RESONANCE, 1976, 8 (08) :426-431
[4]   DETERMINATION OF ENANTIOMERIC PURITY BY AN OPTICALLY ACTIVE NUCLEAR MAGNETIC RESONANCE SHIFT REAGENT OF WIDE APPLICABILITY [J].
FRASER, RR ;
PETIT, MA ;
SAUNDERS, JK .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (22) :1450-&
[5]  
GAMBLIEL H, 1984, J BIOL CHEM, V259, P740
[6]   CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].
GAO, Y ;
HANSON, RM ;
KLUNDER, JM ;
KO, SY ;
MASAMUNE, H ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780
[7]   NEW FURANO-SESQUITERPENOIDS FROM MEDITERRANEAN SPONGES [J].
GUELLA, G ;
MANCINI, I ;
GUERRIERO, A ;
PIETRA, F .
HELVETICA CHIMICA ACTA, 1985, 68 (05) :1276-1282
[8]  
GUERRIERO M, 1984, NATURWISSENSCHAFTEN, V71, P425
[9]   NEW SPONGIAN DITERPENOIDS FROM A GREAT-BARRIER-REEF SPONGE, SPONGIA SP [J].
GUNASEKERA, SP ;
SCHMITZ, FJ .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :1250-1253
[10]  
Harada N, 1983, CIRCULAR DICHROIC SP, P460