ASYMMETRIC-SYNTHESIS OF (2S,3R) BETA-(4-F-3-NO2) PHENYL SERINE, D-(R)-4-METHOXY-3,5-BIS(T)BUTYLDIMETHYLSILOXY PHENYLGLYCINE AND THEIR ASSEMBLAGE TO C-O-D RING OF VANCOMYCIN

被引：46
作者：
ZHU, JP
BOUILLON, JP
SINGH, GP
CHASTANET, J
BEUGELMANS, R
机构：
[1] Institut de Chimie des Substances Naturelles, CNRS
来源：
TETRAHEDRON LETTERS | 1995年 / 36卷 / 39期
关键词：
D O I：
10.1016/0040-4039(95)01409-B
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The asymmetric synthesis of two appropriately functionalized non-proteinogenic amino acids 2 and 3 needed for the total synthesis of vancomycin was described. The assemblage of these amino acids into linear tripeptide followed by biaryl ether formation via intramolecular SNAr reaction led to the fully functionalized C-O-D ring of vancomycin.
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页码：7081 / 7084
页数：4
相关论文
共 30 条
[1]   THE FIRST EXAMPLES OF S(N)AR-BASED MACROCYCLIZATION - SYNTHESIS OF MODEL CARBOXYLATE-BINDING POCKETS OF VANCOMYCIN [J].
BEUGELMANS, R ;
ZHU, JP ;
HUSSON, N ;
BOISCHOUSSY, M ;
SINGH, GP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (04) :439-440
[2]   REDUCTIVE DEPROTECTION OF ARYL ALLYL ETHERS WITH PD(PH3)(4)/NABH4 [J].
BEUGELMANS, R ;
BOURDET, S ;
BIGOT, A ;
ZHU, JP .
TETRAHEDRON LETTERS, 1994, 35 (25) :4349-4350
[3]   A NOVEL SYNTHESIS OF K-13 [J].
BEUGELMANS, R ;
BIGOT, A ;
ZHU, JP .
TETRAHEDRON LETTERS, 1994, 35 (40) :7391-7394
[4]   SNAR-BASED MACROCYCLIZATION - AN APPLICATION TO THE SYNTHESIS OF VANCOMYCIN FAMILY MODELS [J].
BEUGELMANS, R ;
SINGH, GP ;
BOISCHOUSSY, M ;
CHASTANET, J ;
ZHU, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5535-5542
[5]   A NEW ACCESS TO 14-MEMBERED MACROCYCLE - SYNTHESIS OF MODEL F-O-G RING OF TEICOPLANIN [J].
BEUGELMANS, R ;
BOURDET, S ;
ZHU, JP .
TETRAHEDRON LETTERS, 1995, 36 (08) :1279-1282
[6]   PALLADIUM-CATALYZED REDUCTIVE DEPROTECTION OF ALLOC - TRANSPROTECTION AND PEPTIDE-BOND FORMATION [J].
BEUGELMANS, R ;
NEUVILLE, L ;
BOISCHOUSSY, M ;
CHASTANET, J ;
ZHU, JP .
TETRAHEDRON LETTERS, 1995, 36 (18) :3129-3132
[7]   VANCOMYCIN AND RISTOCETIN MODELS - SYNTHESIS VIA THE ULLMANN MACROCYCLIZATION REACTION [J].
BOGER, DL ;
NOMOTO, Y ;
TEEGARDEN, BR .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) :1425-1433
[8]  
BOISCHOUSSY M, 1995, TETRAHEDRON LETT, V36, P4781
[9]   DIASTEREOSELECTIVE STRECKER SYNTHESIS USING ALPHA-PHENYLGLYCINOL AS CHIRAL AUXILIARY [J].
CHAKRABORTY, TK ;
REDDY, GV ;
HUSSAIN, KA .
TETRAHEDRON LETTERS, 1991, 32 (51) :7597-7600
[10]   SYNTHESIS OF PHENOLICALLY LINKED CYCLIC-PEPTIDES [J].
CRIMMIN, MJ ;
BROWN, AG .
TETRAHEDRON LETTERS, 1990, 31 (14) :2021-2024
123