ANOMALY IN THE MODIFIED MOSHER METHOD - ABSOLUTE-CONFIGURATIONS OF SOME MARINE CEMBRANOLIDES

被引:99
作者
KUSUMI, T [1 ]
FUJITA, Y [1 ]
OHTANI, I [1 ]
KAKISAWA, H [1 ]
机构
[1] UNIV TSUKUBA,DEPT CHEM,SAKURA,IBARAKI 305,JAPAN
关键词
D O I
10.1016/0040-4039(91)80650-U
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Utility of the modified Mosher's method is examined by applying it to three marine cembranolides, 2, 3, and 4, with known absolute configurations, and it is concluded that the method can be safely used for the compounds with a sterically unhindered OH group, but care must be taken in applying it to the secondary alcohols with the OH group located in a crowded environment.
引用
收藏
页码:2923 / 2926
页数:4
相关论文
共 17 条
[1]   NOVEL SPONGE-DERIVED AMINO-ACIDS .11. THE ENTIRE ABSOLUTE STEREOCHEMISTRY OF THE BENGAMIDES [J].
ADAMCZESKI, M ;
QUINOA, E ;
CREWS, P .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :240-242
[2]  
FIUD JC, 1977, STEREOCHEMISTRY, V3
[3]   ABSOLUTE-CONFIGURATIONS OF FLAVAN-3-OLS AND 4-ARYLFLAVAN-3-OLS VIA A MODIFIED MOSHER METHOD [J].
HUNDT, AF ;
BURGER, JFW ;
STEYNBERG, JP ;
STEENKAMP, JA ;
FERREIRA, D .
TETRAHEDRON LETTERS, 1990, 31 (35) :5073-5076
[4]  
KASHMAN Y, 1977, ISRAEL J CHEM, V16, P1
[5]   ABSOLUTE STEREOSTRUCTURE OF SWINHOLIDE-A, A POTENT CYTOTOXIC MACROLIDE FROM THE OKINAWAN MARINE SPONGE THEONELLA-SWINHOEI [J].
KITAGAWA, I ;
KOBAYASHI, M ;
KATORI, T ;
YAMASHITA, M ;
TANAKA, J ;
DOI, M ;
ISHIDA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3710-3712
[6]   ARAGUPETROSINE-A, A NEW VASODILATIVE MACROCYCLIC QUINOLIZIDINE ALKALOID FROM AN OKINAWAN MARINE SPONGE XESTOSPONGIA SP [J].
KOBAYASHI, M ;
KAWAZOE, K ;
KITAGAWA, I .
TETRAHEDRON LETTERS, 1989, 30 (31) :4149-4152
[7]   ABSOLUTE-CONFIGURATIONS OF CYTO-TOXIC MARINE CEMBRANOLIDES - CONSIDERATION OF MOSHERS METHOD [J].
KUSUMI, T ;
OHTANI, I ;
INOUYE, Y ;
KAKISAWA, H .
TETRAHEDRON LETTERS, 1988, 29 (37) :4731-4734
[8]  
KUSUMI T, 1988, 16TH IUPAC INT S CHE
[9]  
KUSUMI T, UNPUB TETRAHEDRON LE
[10]   STUDIES ON MARINE NATURAL-PRODUCTS .11. 8,11-EPOXY BRIDGED CEMBRANOLIDE DITERPENE FROM THE SOFT CORAL SINULARIA-FLEXIBILIS [J].
MORI, K ;
SUZUKI, S ;
IGUCHI, K ;
YAMADA, Y .
CHEMISTRY LETTERS, 1983, (10) :1515-1516