FORMAL SYNTHESIS OF (-)-CALCIMYCIN (A-23187) VIA THE 3-METHYL-GAMMA-BUTYROLACTONE APPROACH

被引:21
作者
ZIEGLER, FE
CAIN, WT
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D O I
10.1021/jo00275a019
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
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页码:3347 / 3353
页数:7
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共 31 条
[1]   CRYSTALLINE-STRUCTURE OF THE MAGNESIUM COMPLEX OF CALCIMYCINE (A.23187) [J].
ALLEAUME, M ;
BARRANS, Y .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1985, 63 (12) :3482-3485
[2]   A CONVERGENT GENERAL SYNTHETIC PROTOCOL FOR CONSTRUCTION OF SPIROCYCLIC KETAL IONOPHORES - AN APPLICATION TO THE TOTAL SYNTHESIS OF (-)-A-23187 (CALCIMYCIN) [J].
BOECKMAN, RK ;
CHARETTE, AB ;
ASBEROM, T ;
JOHNSTON, BH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (24) :7553-7555
[3]   STRUCTURE OF A23187, A DIVALENT-CATION IONOPHORE [J].
CHANEY, MO ;
DEMARCO, PV ;
JONES, ND ;
OCCOLOWI.JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (06) :1932-1933
[4]  
CHARETTE AB, 1987, THESIS ROCHESTER
[5]   PRODUCTION BY CONTROLLED BIOSYNTHESIS OF A NOVEL IONOPHORE ANTIBIOTIC, CEZOMYCIN (DEMETHYLAMINO-A23187) [J].
DAVID, L ;
KERGOMARD, A .
JOURNAL OF ANTIBIOTICS, 1982, 35 (10) :1409-1411
[6]   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
[7]   UNSATURATED CARBOHYDRATES .2. 3 REACTIONS LEADING TO UNSATURATED GLYCOPYRANOSIDES [J].
FERRIER, RJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (DEC) :5443-&
[8]   ELABORATION OF THE C(3)-C(12) CARBON FRAGMENT OF CALCIMYCIN (A-23187) - FORMAL TOTAL SYNTHESIS OF CALCIMYCIN [J].
GRIECO, PA ;
WILLIAMS, E ;
TANAKA, H ;
GILMAN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (17) :3537-3539
[9]   A SIMPLE STEREOSELECTIVE VERSION OF CLAISEN REARRANGEMENT LEADING TO TRANS-TRISUBSTITUTED OLEFINIC BONDS . SYNTHESIS OF SQUALENE [J].
JOHNSON, WS ;
WERTHEMANN, L ;
BARTLETT, WR ;
BROCKSOM, TJ ;
LI, TT ;
FAULKNER, DJ ;
PETERSEN, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (03) :741-+
[10]   ACID-BASE PROPERTIES OF IONOPHORE A23187 IN METHANOL WATER SOLUTIONS AND BOUND TO UNILAMELLAR VESICLES OF DIMYRISTOYLPHOSPHATIDYLCHOLINE [J].
KAUFFMAN, RF ;
TAYLOR, RW ;
PFEIFFER, DR .
BIOCHEMISTRY, 1982, 21 (10) :2426-2435