ENANTIOSELECTIVE TOTAL SYNTHESIS OF THE FUNGICIDE BETA-LACTAM ANTIBIOTIC (-)-(2S,5S)-2-(2-HYDROXYETHYL)CLAVAM AND ITS (+)-(2S,5R)-EPIMER

被引:31
作者
HOPPE, D [1 ]
HILPERT, T [1 ]
机构
[1] UNIV GOTTINGEN,INST ORGAN CHEM,D-3400 GOTTINGEN,FED REP GER
关键词
D O I
10.1016/S0040-4020(01)81652-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
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页码:2467 / 2474
页数:8
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共 22 条
[1]   TOTAL SYNTHESIS OF BETA-LACTAMASE INHIBITORS BASED ON THE 4-OXA-1-AZAZABICYCLO[3.2.0]HEPTAN-7-ONE RING-SYSTEM [J].
BENTLEY, PH ;
HUNT, E .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (10) :2222-2227
[2]   STRUCTURES OF 3 NOVEL BETA-LACTAMS ISOLATED FROM STREPTOMYCES-CLAVULIGERUS [J].
BROWN, D ;
EVANS, JR ;
FLETTON, RA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (06) :282-283
[3]  
CLAUSS K, 1974, LIEBIGS ANN CHEM, P539
[4]   TOTAL SYNTHESIS OF (S)-12-HYDROXY-5,8,14-CIS-10-TRANS-EICOSATETRAENOIC ACID (SAMUELSSONS HETE) [J].
COREY, EJ ;
NIWA, H ;
KNOLLE, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (06) :1942-1943
[5]   CLAVALANINE (RO 22-5417), A NEW CLAVAM ANTIBIOTIC FROM STREPTOMYCES-CLAVULIGERUS .4. A STEREORATIONAL SYNTHESIS [J].
DEBERNARDO, S ;
TENGI, JP ;
SASSO, GJ ;
WEIGELE, M .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (19) :3457-3462
[6]   RO-22-5417, A NEW CLAVAM ANTIBIOTIC FROM STREPTOMYCES-CLAVULIGERUS .2. FERMENTATION, ISOLATION AND STRUCTURE [J].
EVANS, RH ;
AX, H ;
JACOBY, A ;
WILLIAMS, TH ;
JENKINS, E ;
SCANNELL, JP .
JOURNAL OF ANTIBIOTICS, 1983, 36 (03) :213-216
[7]  
HILPERT T, 1986, THESIS U GOTTINGEN
[8]  
HOPPE D, 1980, UNPUB
[9]   ON THE SELECTIVITY OF DEPROTECTION OF BENZYL, MPM (4-METHOXYBENZYL) AND DMPM (3,4-DIMETHOXYBENZYL) PROTECTING GROUPS FOR HYDROXY FUNCTIONS [J].
HORITA, K ;
YOSHIOKA, T ;
TANAKA, T ;
OIKAWA, Y ;
YONEMITSU, O .
TETRAHEDRON, 1986, 42 (11) :3021-3028
[10]   SUBSTITUENT EFFECTS IN HYDROGENOLYSIS OF BENZYL ALCOHOL DERIVATIVES OVER PALLADIUM [J].
KIEBOOM, APG ;
DEKREUK, JF ;
VANBEKKU.H .
JOURNAL OF CATALYSIS, 1971, 20 (01) :58-&