CHIRAL SYNTHESIS OF (-)-MESEMBRANOL STARTING FROM D-GLUCOSE

被引:11
作者
CHIDA, N
SUGIHARA, K
OGAWA, S
机构
关键词
D O I
10.1039/c39940000901
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The chiral synthesis of the Sceletium alkaloid, (-)-mesembranol 1 is described; the cyclohexane ring in 1 is prepared in an optically active form from D-glucose using Ferrier's carbocyclisation reaction and the perhydroindole skeleton is effectively constructed by an intramolecular aminomercuration reaction.
引用
收藏
页码:901 / 902
页数:2
相关论文
共 31 条
[1]  
BARTON DHR, 1990, TETRAHEDRON, V46, P215
[2]   AMIDE ACETAL CLAISEN REARRANGEMENT IN THE SYNTHESIS OF MESEMBRANE ALKALOIDS [J].
BAUERMEISTER, S ;
GOUWS, ID ;
STRAUSS, HF ;
VENTER, EMM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (03) :561-565
[3]   BIOMIMETIC SYNTHESIS OF ENANTIOMERICALLY PURE D-MYO-INOSITOL DERIVATIVES [J].
BENDER, SL ;
BUDHU, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) :9883-9885
[4]   TOTAL SYNTHESIS OF ANTIBIOTIC HYGROMYCIN-A [J].
CHIDA, N ;
OHTSUKA, M ;
NAKAZAWA, K ;
OGAWA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) :2976-2983
[5]   TOTAL SYNTHESIS OF (+)-LYCORICIDINE AND ITS 2-EPIMER FROM D-GLUCOSE [J].
CHIDA, N ;
OHTSUKA, M ;
OGAWA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) :4441-4447
[6]   SYNTHESIS OF OPTICALLY-ACTIVE SUBSTITUTED CYCLOHEXENONES FROM CARBOHYDRATES BY CATALYTIC FERRIER REARRANGEMENT [J].
CHIDA, N ;
OHTSUKA, M ;
OGURA, K ;
OGAWA, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (07) :2118-2121
[7]   ENANTIOSPECIFIC SYNTHESIS AND BIOLOGICAL EVALUATION OF SECO ANALOGS OF ANTITUMOR AMARYLLIDACEAE ALKALOIDS [J].
CHRETIEN, F ;
AHMED, SI ;
MASION, A ;
CHAPLEUR, Y .
TETRAHEDRON, 1993, 49 (34) :7463-7478
[8]  
DYONG I, 1986, LIEBIGS ANN CHEM, P551
[9]   SYNTHESIS OF ENANTIOMERICALLY PURE, P-1-TETHERED INOSITOL TETRAKIS(PHOSPHATE) AFFINITY LABELS VIA A FERRIER REARRANGEMENT [J].
ESTEVEZ, VA ;
PRESTWICH, GD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) :9885-9887
[10]   FUNCTIONALIZED CARBOCYCLES FROM CARBOHYDRATES .11. 2 ROUTES TO ENANTIOMERICALLY PURE 3-AMINOINOSOSE DERIVATIVES [J].
FERRIER, RJ ;
STUTZ, AE .
CARBOHYDRATE RESEARCH, 1990, 200 :237-245