Efficient stereoselective synthesis of the epoxyacid fragment of the azinomycins

被引:11
作者
Coleman, RS [1 ]
Sarko, CR [1 ]
Gittinger, JP [1 ]
机构
[1] UNIV S CAROLINA,DEPT CHEM & BIOCHEM,COLUMBIA,SC 29208
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(97)01322-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three concise enantioselective synthetic routes to the C17-C21 epoxyacid segment of the azinomycins are presented and were based on a Sharpless asymmetric epoxidation/kinetic resolution of racemic allylic alcohol (+/-)-3 that occurred with reversal of the expected sense of enantioselection. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:5917 / 5920
页数:4
相关论文
共 34 条
[21]   A CONVENIENT STEREOSELECTIVE SYNTHESIS OF 1,2,3-AMINODIOLS FROM ALPHA-AMINO-ACIDS [J].
LULY, JR ;
HSIAO, CN ;
BAMAUNG, N ;
PLATTNER, JJ .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) :6109-6112
[22]   KINETIC RESOLUTION OF RACEMIC ALLYLIC ALCOHOLS BY ENANTIOSELECTIVE EPOXIDATION - A ROUTE TO SUBSTANCES OF ABSOLUTE ENANTIOMERIC PURITY [J].
MARTIN, VS ;
WOODARD, SS ;
KATSUKI, T ;
YAMADA, Y ;
IKEDA, M ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (20) :6237-6240
[23]   HIGHLY CONVERGENT APPROACH TO THE SYNTHESIS OF THE EPOXY-AMIDE FRAGMENT OF THE AZINOMYCINS [J].
MORAN, EJ ;
ARMSTRONG, RW .
TETRAHEDRON LETTERS, 1991, 32 (31) :3807-3810
[24]   DEHYDROAMINO ACID-DERIVATIVES FROM D-ARABINOSE AND L-SERINE - SYNTHESIS OF MODELS FOR THE AZINOMYCIN ANTITUMOR ANTIBIOTICS [J].
MORAN, EJ ;
TELLEW, JE ;
ZHAO, ZC ;
ARMSTRONG, RW .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) :7848-7859
[25]   AZINOMYCIN-A AND AZINOMYCIN-B, NEW ANTITUMOR ANTIBIOTICS .1. PRODUCING ORGANISM, FERMENTATION, ISOLATION, AND CHARACTERIZATION [J].
NAGAOKA, K ;
MATSUMOTO, M ;
OONO, J ;
YOKOI, K ;
ISHIZEKI, S ;
NAKASHIMA, T .
JOURNAL OF ANTIBIOTICS, 1986, 39 (11) :1527-1532
[26]   SYNTHETIC STUDIES ON CARZINOPHILIN-A - SYNTHESIS OF THE OPTICALLY-ACTIVE C.1-C.18 SEGMENT [J].
SHIBUYA, M .
TETRAHEDRON LETTERS, 1983, 24 (11) :1175-1178
[27]   SYNTHETIC STUDIES TOWARD AZINOMYCINS-A AND AZINOMYCINS-B - SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF THE MINOR COMPONENT ISOLATED FROM AZINOMYCINS PRODUCING STRAIN [J].
SHIBUYA, M ;
TERAUCHI, H .
TETRAHEDRON LETTERS, 1987, 28 (23) :2619-2622
[28]   SIMPLE AND EFFICIENT ACCESS TO THE LEFT-HAND SEGMENT OF AZINOMYCINS [J].
SHISHIDO, K ;
OMODANI, T ;
SHIBUYA, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (16) :2053-2054
[29]   INVERSION OF ENANTIOSELECTIVITY IN THE KINETIC RESOLUTION MODE OF THE KATSUKI-SHARPLESS ASYMMETRIC EPOXIDATION REACTION [J].
TAKANO, S ;
IWABUCHI, Y ;
OGASAWARA, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (07) :2786-2787
[30]   KATSUKI-SHARPLESS ASYMMETRIC EPOXIDATION OF ALLYLIC-HOMOALLYLIC ALCOHOLS SHARING THE CENTRAL OLEFINIC BOND [J].
TAKANO, S ;
SETOH, M ;
TAKAHASHI, M ;
OGASAWARA, K .
TETRAHEDRON LETTERS, 1992, 33 (37) :5365-5368