PSICOPLANOCIN-A - A SYNTHETIC CARBOCYCLIC NUCLEOSIDE WITH THE COMBINED STRUCTURAL FEATURES OF NEPLANOCIN-A AND PSICOFURANINE

被引:6
作者
MARQUEZ, VE
BODENTEICH, M
机构
[1] Laboratory of Medicinal Chemistry, DTP, DCT, National Cancer Institute, NIH, Bethesda
来源
NUCLEOSIDES & NUCLEOTIDES | 1991年 / 10卷 / 1-3期
关键词
D O I
10.1080/07328319108046467
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Psicoplanocin A represents the first known example of a carbocyclic ketohexose nucleoside. It was synthesized in 8 steps from racemic cyclopentenone 5 which in turn is available from D-ribonolactone.
引用
收藏
页码:311 / 314
页数:4
相关论文
共 11 条
[1]  
ABEDIN ZU, 1983, NUCLEOS NUCLEOT, V2, P257
[2]   DIMETHYLOXOSULFONIUM METHYLIDE ((CH3)2SOCH2) AND DIMETHYLSULFONIUM METHYLIDE ((CH3)2SCH2) FORMATION AND APPLICATION TO ORGANIC SYNTHESIS [J].
COREY, EJ ;
CHAYKOVSKY, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) :1353-+
[3]   SYNTHETIC METHODS .19. LEWIS ACID-CATALYZED CONVERSION OF ALKENES AND ALCOHOLS TO AZIDES [J].
HASSNER, A ;
FIBIGER, R ;
ANDISIK, D .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (22) :4237-4244
[4]   TOTAL SYNTHESIS OF (-)-NEPLANOCIN-A [J].
MARQUEZ, VE ;
LIM, MI ;
TSENG, CKH ;
MARKOVAC, A ;
PRIEST, MA ;
KHAN, MS ;
KASKAR, B .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) :5709-5714
[5]   CARBOCYCLIC NUCLEOSIDES [J].
MARQUEZ, VE ;
LIM, MI .
MEDICINAL RESEARCH REVIEWS, 1986, 6 (01) :1-40
[6]  
MEDICH JR, 1987, TETRAHEDRON LETT, V28, P4143
[7]  
NICHOL CA, 1975, HDB EXP PHARM 2, V38, P434
[8]   EFFICIENT SYNTHESIS OF DERIVATIVES OF TRIBUTYLSTANNYLMETHANOL [J].
SEITZ, DE ;
CARROLL, JJ ;
CARTAYA, CP ;
LEE, SH ;
ZAPATA, A .
SYNTHETIC COMMUNICATIONS, 1983, 13 (02) :129-134
[9]   STANNYLATION-DESTANNYLATION - PREPARATION OF ALPHA-ALKOXY ORGANOLITHIUM REAGENTS AND SYNTHESIS OF DENDROLASIN VIA A CARBINYL CARBANION EQUIVALENT [J].
STILL, WC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (05) :1481-1487
[10]  
SUHADOLNIK RJ, 1970, NUCLEOSIDE ANTIBIOTI, P105