STEREOSELECTIVE TOTAL SYNTHESIS OF POLYETHER IONOPHORE ANTIBIOTICS, ISOLASALOCID-A AND LASALOCID-A .1. STEREOCONTROLLED CONSTRUCTION OF THE C-RINGS (C-18-C-24) BY ACID-CATALYZED CYCLIZATION OF P-METHOXYPHENYLALLYL ALCOHOLS

被引:7
作者
HORITA, K
NODA, I
TANAKA, K
MIURA, T
OIKAWA, Y
YONEMITSU, O
机构
[1] Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo
关键词
POLYETHER ANTIBIOTIC; TOTAL SYNTHESIS; STEREOSELECTIVE SYNTHESIS; TETRAHYDROFURAN; TETRAHYDROPYRAN; ACID-CATALYZED CYCLIZATION;
D O I
10.1016/S0040-4020(01)87184-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The C18-C24 subunits (11, 12) of isolasalocid A (9) and lasalocid A (10) were synthesized stereoselectively via construction of the tetrahydrofuran and tetrahydropyran rings by acid-catalyzed cyclization of the corresponding p-methoxyphenylallyl alcohols (18, 25).
引用
收藏
页码:5979 / 5996
页数:18
相关论文
共 30 条
[1]   HIGH DIASTEREOFACE SELECTION IN AN ESTER ENOLATE ADDITION TO ALPHA-ALKOXY ALDEHYDES - STEREOSELECTIVE SYNTHESIS OF ALPHA-METHYLENE-BETA-HYDROXY-GAMMA-ALKOXY ESTERS [J].
BANFI, L ;
BERNARDI, A ;
COLOMBO, L ;
GENNARI, C ;
SCOLASTICO, C .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (20) :3784-3790
[2]  
BERGER J, 1951, J AM CHEM SOC, V73, P5925
[4]  
CARDILLO G, 1990, TETRAHEDRON, V46, P321
[5]   TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC IONOMYCIN [J].
EVANS, DA ;
DOW, RL ;
SHIH, TL ;
TAKACS, JM ;
ZAHLER, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) :5290-5313
[6]   TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC X-206 [J].
EVANS, DA ;
BENDER, SL ;
MORRIS, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2506-2526
[7]   POLYETHER ANTIBIOTICS SYNTHESIS - TOTAL SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE IONOPHORE-A-23187 [J].
EVANS, DA ;
SACKS, CE ;
KLESCHICK, WA ;
TABER, TR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (22) :6789-6791
[8]   SYNTHETIC STUDIES IN THE LYSOCELLIN FAMILY OF POLYETHER ANTIBIOTICS - THE TOTAL SYNTHESIS OF FERENSIMYCIN-B [J].
EVANS, DA ;
POLNIASZEK, RP ;
DEVRIES, KM ;
GUINN, DE ;
MATHRE, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7613-7630
[9]   SYNTHETIC STUDIES ON POLYETHER ANTIBIOTICS .6. TOTAL SYNTHESIS OF MONENSIN .3. STEREOCONTROLLED TOTAL SYNTHESIS OF MONENSIN [J].
FUKUYAMA, T ;
AKASAKA, K ;
KARANEWSKY, DS ;
WANG, CLJ ;
SCHMID, G ;
KISHI, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (01) :262-263
[10]   CHIRAL SYNTHESIS OF POLYKETIDE-NATURAL PRODUCTS .40. TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC LYSOCELLIN .2. STEREOCONTROLLED SYNTHESIS OF THE C10-C23 FRAGMENT AND ITS ALDOL CONDENSATION WITH THE C1-C9 FRAGMENT TO COMPLETE THE TOTAL SYNTHESIS OF LYSOCELLIN [J].
HORITA, K ;
TANAKA, K ;
INOUE, T ;
YONEMITSU, O .
TETRAHEDRON LETTERS, 1992, 33 (38) :5541-5544