SYNTHESIS OF RING-C AROMATIC STEROIDS

被引:9
作者
DALZELL, HC [1 ]
MANMADE, A [1 ]
MASTROCOLA, AR [1 ]
RAZDAN, RK [1 ]
机构
[1] SISA INC, CAMBRIDGE, MA 02138 USA
关键词
D O I
10.1021/jo01328a026
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical multistep synthetic route to ring-C aromatic testosterone analogue 8b from 1, 7-dihydroxynaphthalene (1a) is described. The key intermediate in this sequence is the diketone 7. The synthesis of 8b from 7 was achieved by reduction with sodium borohydride under carefully controlled conditions followed by separation using high-pressure liquid chromatography. Studies with europium shift reagent were used for assigning the β stereochemistry for the 17-hydroxy group of 8b. © 1979, American Chemical Society. All rights reserved.
引用
收藏
页码:2457 / 2461
页数:5
相关论文
共 23 条
[1]   USE OF LANTHANIDE NUCLEAR MAGNETIC-RESONANCE SHIFT REAGENTS IN DETERMINATION OF MOLECULAR CONFIGURATION [J].
ARMITAGE, IM ;
HALL, LD ;
MARSHALL, AG ;
WERBELOW, LG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (05) :1437-1443
[2]  
BIRCH AJ, 1967, TETRAHEDRON LETT, P857
[3]   18-NORPREGNA-8,11,13-TRIENES .2. PREPARATION FROM "17BETA-METHYL-17ALPHA-PREGN-13-ENES [J].
CAMPBELL, AC ;
MAIDMENT, MS ;
PICK, JH ;
STEVENSON, DFM ;
WOODS, GF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (02) :163-171
[4]  
CHAKRAVA.KK, 1974, INDIAN J CHEM, V12, P275
[5]  
CHATTERJEE A, 1969, TETRAHEDRON LETT, P76
[6]  
CHATTERJEE A, 1970, CHEM COMMUN, P618
[7]   PARAMAGNETIC INDUCED SHIFTS IN PROTON MAGNETIC RESONANCE SPECTRA OF ALCOHOLS USING TRIS(DIPIVALOMETHANATO)EUROPIUM(III) [J].
DEMARCO, PV ;
ELZEY, TK ;
LEWIS, RB ;
WENKERT, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (19) :5734-+
[8]   TRIS(DIPIVALOMETHANATO)EUROPIUM(III) - A SHIFT REAGENT FOR USE IN PROTON MAGNETIC RESONANCE ANALYSIS OF STEROIDS AND TERPENOIDS [J].
DEMARCO, PV ;
ELZEY, TK ;
LEWIS, RB ;
WENKERT, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (19) :5737-+
[9]   UNSATURATED STEROIDS .9. SYNTHESIS OF SOME AROMATIC RING-C STEROIDS [J].
EDMUNDS, R ;
MIDGLEY, JM ;
TAGG, LG ;
WILKINS, BJ ;
WHALLEY, WB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (01) :76-80
[10]  
GROVE JF, 1969, J CHEM SOC C, P594