First total synthesis of an exceptionally potent antitumor saponin, OSW-1

被引:139
作者
Deng, SJ [1 ]
Yu, B [1 ]
Lou, Y [1 ]
Hui, YZ [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1021/jo981685c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
OSW-1 (1), an acylated disaccharide cholestane saponin from Ornithogalum saudersiae with exceptionally potent antitumor activity, was first synthesized from commercially available dehydroisoandrosterone, L-arabinose, and D-xylose in total 27 steps with the longest linear sequence of 14 steps and in 6% yield.
引用
收藏
页码:202 / 208
页数:7
相关论文
共 45 条
[1]   NMR-SPECTROSCOPY IN THE STRUCTURAL ELUCIDATION OF OLIGOSACCHARIDES AND GLYCOSIDES [J].
AGRAWAL, PK .
PHYTOCHEMISTRY, 1992, 31 (10) :3307-3330
[3]   A NEW SYNTHESIS OF D-ERYTHROSE DERIVATIVES FROM D-ARABINOSE [J].
BALLOU, CE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (01) :165-166
[4]   STEREOSELECTIVE INTRODUCTION OF STEROID SIDE-CHAINS AT C(17) AND C(20) [J].
BATCHO, AD ;
BERGER, DE ;
DAVOUST, SG ;
WOVKULICH, PM ;
USKOKOVIC, MR .
HELVETICA CHIMICA ACTA, 1981, 64 (05) :1682-1687
[5]   16-HYDROXYLATED STEROIDS .6. THE SYNTHESIS OF THE 16-ALPHA-HYDROXY DERIVATIVES OF 9-ALPHA-SUBSTITUTED STEROIDS [J].
BERNSTEIN, S ;
LENHARD, RH ;
ALLEN, WS ;
HELLER, M ;
LITTELL, R ;
STOLAR, SM ;
FELDMAN, LI ;
BLANK, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (07) :1689-1696
[6]   16-HYDROXYLATED STEROIDS .8. 5-BETA-DIHYDROCORTISONE APPROACH TO THE SYNTHESIS OF TRIAMCINOLONE [J].
BERNSTEIN, S ;
LITTELL, R .
JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (03) :429-431
[7]   16-HYDROXYLATED STEROIDS .19. SYNTHESIS OF 16ALPHA-HYDROXY-19-NORHYDROCORTISONE [J].
BROWN, JJ ;
BERNSTEIN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (12) :5033-&
[8]   SMALL-RING COMPOUNDS .21. 3-METHYLENECYCLOBUTANONE AND RELATED COMPOUNDS [J].
CASERIO, FF ;
ROBERTS, JD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (21) :5837-5840
[9]  
Collins P.M., 1995, MONOSACCHARIDES THEI, P22
[10]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156