Concerning the synthesis of the elusive anti,anti-dipropionate stereotriad via the crotylation of β-hydroxy α-methyl aldehydes with (Z)-crotyltrifluorosilane.: Application to the synthesis of the C(7)-C(16) segment of zincophorin

被引:52
作者
Chemler, SR
Roush, WR [1 ]
机构
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
[2] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
关键词
D O I
10.1021/jo980387c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[No abstract available]
引用
收藏
页码:3800 / 3801
页数:2
相关论文
共 21 条
[1]   THE STRUCTURE AND ABSOLUTE STEREOCHEMISTRY OF ZINCOPHORIN (ANTIBIOTIC M144255) - A MONOBASIC CARBOXYLIC-ACID IONOPHORE HAVING A REMARKABLE SPECIFICITY FOR DIVALENT-CATIONS [J].
BROOKS, HA ;
GARDNER, D ;
POYSER, JP ;
KING, TJ .
JOURNAL OF ANTIBIOTICS, 1984, 37 (11) :1501-1504
[2]   TOTAL SYNTHESIS OF ZINCOPHORIN [J].
DANISHEFSKY, SJ ;
SELNICK, HG ;
ZELLE, RE ;
DENINNO, MP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (13) :4368-4378
[3]  
Gewald R, 1996, SYNTHESIS-STUTTGART, P111
[4]  
GRAFE U, 1984, J ANTIBIOT, V37, P836
[5]  
HOFFMANN RW, 1994, SYNTHESIS-STUTTGART, P629
[6]   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
[7]   STEREOSELECTIVE SYNTHESIS OF ALCOHOLS .29. ADDITION OF (ALPHA-METHOXYCROTYL)BORONATES TO ALDEHYDES [J].
HOFFMANN, RW ;
DRESELY, S .
CHEMISCHE BERICHTE, 1989, 122 (05) :903-909
[8]   Double-stereodifferentiating crotylation reactions with chiral (E)-crotylsilanes. Evaluation of a new approach for the synthesis of polypropionate-derived natural products [J].
Jain, NF ;
Takenaka, N ;
Panek, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (49) :12475-12476
[9]   CHEMISTRY OF ORGANOSILICON COMPOUNDS .234. REGIOSPECIFIC AND HIGHLY STEREOSELECTIVE ALLYLATION OF ALDEHYDES WITH ALLYLTRIFLUOROSILANE ACTIVATED BY FLUORIDE IONS [J].
KIRA, M ;
KOBAYASHI, M ;
SAKURAI, H .
TETRAHEDRON LETTERS, 1987, 28 (35) :4081-4084
[10]   CHEMISTRY OF ORGANOSILICON COMPOUNDS .259. HIGHLY STEREOSELECTIVE ALLYLATION OF ALDEHYDES WITH PENTACOORDINATE ALLYLSILICATES IN HYDROXYLIC MEDIA - DISCRIMINATION BETWEEN LINEAR AND ALPHA-BRANCHED ALKANALS [J].
KIRA, M ;
SATO, K ;
SAKURAI, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (01) :257-260