SYNTHESIS AND OXIDATIVE CLEAVAGE OF THE MAJOR EQUILIBRIUM PRODUCTS OF ASCOMYCIN AND FK-506

被引:12
作者
BAUMANN, K
OBERHAUSER, B
GRASSBERGER, MA
HAIDL, G
SCHULZ, G
机构
[1] Department of Dermatology, A-1235 Vienna
关键词
D O I
10.1016/0040-4039(95)00220-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ascomycin and FK 506 are converted into the 9-ketal isomers in high yields by simple treatment with Lewis acids. The structure of the 9-ketal isomer was confirmed by oxidative cleavage.
引用
收藏
页码:2231 / 2234
页数:4
相关论文
共 14 条
[1]   CHEMISTRY OF FK-506 - BENZILIC ACID REARRANGEMENT OF THE TRICARBONYL SYSTEM [J].
ASKIN, D ;
REAMER, RA ;
JONES, TK ;
VOLANTE, RP ;
SHINKAI, I .
TETRAHEDRON LETTERS, 1989, 30 (06) :671-674
[2]   Oxidative cleavage of alpha-keto acids and alpha-keto alcohols by means of lead tetraacetate [J].
Baer, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 :1597-1606
[3]  
COLEMAN RS, 1989, HETEROCYCLES, V28, P157
[4]   CLEAVAGE AND REARRANGEMENT OF ETHERS WITH BASE .2. REACTION OF THE BENZHYDRYL AND TRITYL ETHERS OF BENZOIN WITH POTASSIUM HYDROXIDE [J].
CURTIN, DY ;
LESKOWITZ, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (06) :2633-2636
[5]   ON THE REMARKABLE PROPENSITY FOR CARBON CARBON BOND-CLEAVAGE REACTIONS IN THE C8-C10 REGION OF FK-506 [J].
FISHER, MJ ;
CHOW, K ;
VILLALOBOS, A ;
DANISHEFSKY, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2900-2907
[6]  
FRANCIS PG, 1994, J ANTIBIOT, V47, P806
[7]  
GRASSBERGER MA, 1993, CURRENT OPINION THER, P931
[8]  
HO TL, 1972, SYNTH-INT J METHODS, P560
[9]   FK-506, A NOVEL IMMUNOSUPPRESSANT ISOLATED FROM A STREPTOMYCES .1. FERMENTATION, ISOLATION, AND PHYSICOCHEMICAL AND BIOLOGICAL CHARACTERISTICS [J].
KINO, T ;
HATANAKA, H ;
HASHIMOTO, M ;
NISHIYAMA, M ;
GOTO, T ;
OKUHARA, M ;
KOHSAKA, M ;
AOKI, H ;
IMANAKA, H .
JOURNAL OF ANTIBIOTICS, 1987, 40 (09) :1249-1255
[10]   STUDIES ON THE CHEMISTRY OF RAPAMYCIN - NOVEL TRANSFORMATIONS UNDER LEWIS-ACID CATALYSIS [J].
LUENGO, JI ;
KONIALIAN, AL ;
HOLT, DA .
TETRAHEDRON LETTERS, 1993, 34 (06) :991-994