STEREOSPECIFIC SYNTHESIS OF AMINOCYCLITOLS VIA CYCLOADDITIONS OF UNSYMMETRICAL, OPTICALLY PURE DIENES - CONDURAMINE-A-1 AND DIHYDROCONDURAMINE-A-1

被引:78
作者
HUDLICKY, T
OLIVO, HF
机构
[1] Department of Chemistry, Virginia Polytechnic Institute, State University, Blacksburg
基金
美国国家卫生研究院;
关键词
D O I
10.1016/0040-4039(91)80757-W
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereospecific synthesis of Conduramine A-1 and Dihydroconduramine A-1 has been achieved by a fully regio- and stereospecific hetero Diels-Alder cycloaddition of a nitrosyl derivative and homochiral 1-halocyclohexadiene diols obtained by microbial oxidation of halobenzenes.
引用
收藏
页码:6077 / 6080
页数:4
相关论文
共 28 条
[1]   CONDURITOLS AND RELATED-COMPOUNDS [J].
BALCI, M ;
SUTBEYAZ, Y ;
SECEN, H .
TETRAHEDRON, 1990, 46 (11) :3715-3742
[2]  
Boger D. L., 1987, HETERO DIELS ALDER M
[3]   OXIDATION OF HYDROXAMIC ACIDS [J].
BOYLAND, E ;
NERY, R .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (03) :354-&
[4]   SYNTHESIS OF CHIRAL AMINOCYCLITOLS VIA EPOXYEPIMINATION [J].
BRAUN, H ;
BURGER, W ;
KRESZE, G ;
SCHMIDTCHEN, FP ;
VAERMAN, JL ;
VIEHE, HG .
TETRAHEDRON-ASYMMETRY, 1990, 1 (06) :403-415
[5]   TOTAL SYNTHESIS OF DL-CEPHALOTAXINE - THE 1ST EXAMPLE OF AN INTRAMOLECULAR 4 + 2 CYCLO-ADDITION WHERE THE DIENOPHILE HAS BEEN DELIVERED FROM THE FACE OPPOSITE TO THE TETHERING MOIETY [J].
BURKHOLDER, TP ;
FUCHS, PL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2341-2342
[6]   [4 + 2], [2 + 2], AND CARBENE ADDITION-REACTIONS INVOLVING CYCLOHEXA-3,5-DIENE-CIS-1,2-DIOL DERIVATIVES [J].
DOWNING, W ;
LATOUCHE, R ;
PITTOL, CA ;
PRYCE, RJ ;
ROBERTS, SM ;
RYBACK, G ;
WILLIAMS, JO .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (09) :2613-2615
[7]   PREPARATION AND SOME PROPERTIES OF STABLE AND CARBON-14 AND TRITIUM-LABELED SHORT-CHAIN ALIPHATIC HYDROXAMIC ACIDS [J].
FISHBEIN, WN ;
DALY, J ;
STREETER, CL .
ANALYTICAL BIOCHEMISTRY, 1969, 28 (1-3) :13-&
[8]  
HUDLICKY T, 1990, SYNLETT, P159
[9]   EFFICIENT AND ENANTIODIVERGENT SYNTHESIS OF (+)-PINITOL AND (-)-PINITOL [J].
HUDLICKY, T ;
PRICE, JD ;
RULIN, F ;
TSUNODA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (25) :9439-9440
[10]  
HUDLICKY T, 1990, SYNLETT, P309