A HIGHLY CONVERGENT ASYMMETRIC-SYNTHESIS OF THE C(19)-C(27) SEGMENT OF RIFAMYCIN-S - AN APPLICATION OF ENANTIODIFFERENTIATING ACETALIZATION WITH MENTHONE

被引:46
作者
HARADA, T
KAGAMIHARA, Y
TANAKA, S
SAKAMOTO, K
OKU, A
机构
[1] Department of Chemistry, Kyoto Institute of Technology, Kyoto, 606, Matsugasaki, Sakyo-ku
关键词
D O I
10.1021/jo00032a004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An enantiodifferentiating transformation of 1,3-alkanediols by kinetic acetalization with menthone is developed and used in a highly convergent asymmetric synthesis of the C(19)-C(27) segment of the ansa chain of rifamycin S.
引用
收藏
页码:1637 / 1639
页数:3
相关论文
共 30 条
[1]   ORGANOBORANES .53. A HIGH-FIELD VARIABLE-TEMPERATURE H-1 AND B-11 NMR-STUDY OF THE EFFECTS OF SOLVENT AND STRUCTURE ON REACTIVITY IN ALLYLBORATION [J].
BROWN, HC ;
RACHERLA, US ;
PELLECHIA, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1868-1874
[2]  
BRUFANI M, 1977, TOPICS ANTIBIOT CHEM, V1, P91
[3]  
COREY EJ, 1979, TETRAHEDRON LETT, P335
[4]   EXPEDITIOUS SYNTHESIS OF THE POLYPROPIONATE SECTOR OF RIFAMYCIN-S BY REITERATIVE DIENE ALDEHYDE CYCLOCONDENSATION REACTIONS [J].
DANISHEFSKY, SJ ;
MYLES, DC ;
HARVEY, DF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :862-867
[5]   NEW STRATEGY FOR CARBOHYDRATE-BASED SYNTHESES OF MULTICHIRAL ARRAYS - PYRANOSIDIC HOMOLOGATION .3. [J].
FRASERREID, B ;
MAGDZINSKI, L ;
MOLINO, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (03) :731-734
[6]   ASSEMBLY OF THE C19-C29 ALIPHATIC SEGMENT OF RIFAMYCIN S FROM D-GLUCOSE BY THE CHIRON APPROACH [J].
HANESSIAN, S ;
POUGNY, JR ;
BOESSENKOOL, IK .
TETRAHEDRON, 1984, 40 (08) :1289-1301
[7]   STEREOCHEMICAL CONTROL OF CONSECUTIVE STEREOGENIC CENTERS BY INTRAMOLECULAR HYDROBORATION OF DIALKENYL CARBINOL DERIVATIVES [J].
HARADA, T ;
MATSUDA, Y ;
WADA, I ;
UCHIMURA, J ;
OKU, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (01) :21-22
[8]   ENANTIODIFFERENTIATING TRANSFORMATION OF PROCHIRAL 1,3,5-PENTANETRIOLS CONTROLLED BY INTRAMOLECULAR VANDERWAALS ATTRACTIONS [J].
HARADA, T ;
WADA, I ;
UCHIMURA, JJ ;
INOUE, A ;
TANAKA, S ;
OKU, A .
TETRAHEDRON LETTERS, 1991, 32 (09) :1219-1222
[9]  
HARADA T, IN PRESS J ORG CHEM
[10]   STEREOSELECTIVE SYNTHESES OF BUILDING-BLOCKS WITH 3 CONSECUTIVE STEREOGENIC CENTERS - IMPORTANT PRECURSORS OF POLYKETIDE NATURAL-PRODUCTS [J].
HOFFMANN, RW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (06) :489-503