TOTAL SYNTHESIS OF (+)-LYCORICIDINE AND ITS 2-EPIMER FROM D-GLUCOSE

被引:81
作者
CHIDA, N [1 ]
OHTSUKA, M [1 ]
OGAWA, S [1 ]
机构
[1] KEIO UNIV, FAC SCI & TECHNOL,DEPT APPL CHEM,3-14-1 HIYOSHI, KOHOKU KU, YOKOHAMA, KANAGAWA 223, JAPAN
关键词
D O I
10.1021/jo00068a045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereoselective total synthesis of antimitotic alkaloid (+)-lycoricidine (1) and its 2-epimer (30) was accomplished starting from D-glucose. The key steps in this synthesis are (i) a catalytic version of the Ferrier rearrangement for the preparation of the optically active substituted cyclohexenone (the C-ring of lycoricidine) and (ii) a Pd-catalyzed intramolecular Heck-typE, reaction for construction of the phenanthridone skeleton. A preliminary biological assay revealed that the stereochemistry at the 2-position of lycoricidine plays an important role in its cytotoxic activity.
引用
收藏
页码:4441 / 4447
页数:7
相关论文
共 72 条
  • [1] INTRAMOLECULAR ALKENE ARYLATIONS FOR RAPID ASSEMBLY OF POLYCYCLIC SYSTEMS CONTAINING QUATERNARY CENTERS - A NEW SYNTHESIS OF SPIROOXINDOLES AND OTHER FUSED AND BRIDGED RING-SYSTEMS
    ABELMAN, MM
    OH, T
    OVERMAN, LE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) : 4130 - 4133
  • [2] NARCICLASINE-4-O-BETA-D-GLUCOPYRANOSIDE, A GLUCOSYLOXY AMIDIC PHENANTHRIDONE DERIVATIVE FROM PANCRATIUM-MARITIMUM
    ABOUDONIA, AH
    DEGIULIO, A
    EVIDENTE, A
    GABER, M
    HABIB, AA
    LANZETTA, R
    ELDIN, AAS
    [J]. PHYTOCHEMISTRY, 1991, 30 (10) : 3445 - 3448
  • [3] BARTON DHR, 1990, TETRAHEDRON, V46, P215
  • [4] SYNTHETIC METHODS FOR THE PREPARATION OF D-PSEUDO-SUGARS AND L-PSEUDO-SUGARS FROM D-GLUCOSE
    BARTON, DHR
    GERO, SD
    CLEOPHAX, J
    MACHADO, AS
    QUICLETSIRE, B
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (17) : 1184 - 1186
  • [5] FUNCTIONALIZED CARBOCYCLES FROM CARBOHYDRATES .8. UNSATURATED CARBOHYDRATES .28. OBSERVATIONS ON THE CONVERSION OF 6-DEOXYHEX-5-ENOPYRANOSYL COMPOUNDS INTO 2-DEOXYINOSOSE DERIVATIVES
    BLATTNER, R
    FERRIER, RJ
    HAINES, SR
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11): : 2413 - 2416
  • [6] CRYSTALLINE PSEUDO-ALPHA-D-GLUCOPYRANOSE
    BLATTNER, R
    FERRIER, RJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (13) : 1008 - 1009
  • [7] NARCICLASINE - AN ANTIMITOTIC SUBSTANCE FROM NARCISSUS BULBS
    CERIOTTI, G
    [J]. NATURE, 1967, 213 (5076) : 595 - &
  • [8] STEREOSELECTIVE TOTAL SYNTHESIS OF (+)-LYCORICIDINE
    CHIDA, N
    OHTSUKA, M
    OGAWA, S
    [J]. TETRAHEDRON LETTERS, 1991, 32 (35) : 4525 - 4528
  • [9] TOTAL SYNTHESIS OF ANTIBIOTIC HYGROMYCIN-A
    CHIDA, N
    OHTSUKA, M
    NAKAZAWA, K
    OGAWA, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) : 2976 - 2983
  • [10] SYNTHESIS OF OPTICALLY-ACTIVE SUBSTITUTED CYCLOHEXENONES FROM CARBOHYDRATES BY CATALYTIC FERRIER REARRANGEMENT
    CHIDA, N
    OHTSUKA, M
    OGURA, K
    OGAWA, S
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (07) : 2118 - 2121