STEREOSPECIFIC PICTET-SPENGLER REACTION - SYNTHESIS OF CIS (+)-(1S,12BR)-1-AMINOINDOLOQUINOLIZIDINE FROM A PURE ALPHA-(S)-AMINOALDEHYDE DERIVATIVE

被引:24
作者
MELNYK, P [1 ]
DUCROT, P [1 ]
THAL, C [1 ]
机构
[1] INST CHIM SUBST NAT,CNRS,AVE TERRASSE,F-91198 GIF SUR YVETTE,FRANCE
关键词
D O I
10.1016/S0040-4020(01)96265-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pictet-Spengler reaction provides cis (+)-1-(S)-aminoindolo[2,3-a]quinolizidine in an enantio- and diastereoselective manner, using an alpha-aminoaldehyde derived from L-glutamic acid.
引用
收藏
页码:8589 / 8596
页数:8
相关论文
共 11 条
  • [1] DIASTEREOSELECTIVITY AND ENANTIOSELECTIVITY IN THE PICTET-SPENGLER REACTION
    BAILEY, PD
    HOLLINSHEAD, SP
    MCLAY, NR
    MORGAN, K
    PALMER, SJ
    PRINCE, SN
    REYNOLDS, CD
    WOOD, SD
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (04): : 431 - 439
  • [2] BAILEY PD, 1987, J CHEM RES S, P20
  • [3] FEHRENTZ JA, 1983, SYNTHESIS-STUTTGART, P676
  • [4] FISCHER LE, 1990, ORG PREP P INT, V22, P399
  • [5] HUSSON HP, 1973, B SOC CHIM FR II-CH, P2013
  • [6] ELECTROPHILIC SUBSTITUTION IN INDOLES .4. CYCLIZATION OF INDOLYLBUTANOL TO TETRAHYDROCARBAZOLE
    JACKSON, AH
    NAIDOO, B
    SMITH, P
    [J]. TETRAHEDRON, 1968, 24 (19) : 6119 - +
  • [7] OPTICALLY-ACTIVE N-PROTECTED ALPHA-AMINO ALDEHYDES IN ORGANIC-SYNTHESIS
    JURCZAK, J
    GOLEBIOWSKI, A
    [J]. CHEMICAL REVIEWS, 1989, 89 (01) : 149 - 164
  • [8] TOTAL SYNTHESIS OF (-)-EUDISTOMIN L AND (-)-DEBROMOEUDISTOMIN L
    NAKAGAWA, M
    LIU, JJ
    HINO, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) : 2721 - 2722
  • [9] PILLEBOUEMELYNK P, 1992, THESIS U PARIS 7
  • [10] SCHMITT P, 1993, MED CHEM RES, V3, P24