Intramolecular Mannich reaction in the asymmetric synthesis of polysubstituted piperidines: Concise synthesis of the dendrobate alkaloid (+)-241D and its C-4 epimer

被引:114
作者
Davis, FA [1 ]
Chao, B [1 ]
Rao, A [1 ]
机构
[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
关键词
D O I
10.1021/ol0164839
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
GRAPHICS The intramolecular Mannich reaction of delta -amino beta -keto esters with aldehydes and ketones is a new methodology for the synthesis of polysubstituted piperidines and is illustrated by the concise asymmetric synthesis of the dendrobate alkaloid (+)-241D and its C-4 epimer.
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页码:3169 / 3171
页数:3
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共 19 条
  • [1] STUDIES ON CONFORMATION .1. PREPARATION AND STEREOCHEMISTRY OF SOME 4-PIPERIDINOLS
    BALASUBRAMANIAN, M
    PADMA, N
    [J]. TETRAHEDRON, 1963, 19 (12) : 2135 - &
  • [2] Enzymatic route to chiral, nonracemic cis-2,6- and cis,cis-2,4,6-substituted piperidines. Synthesis of (+)-dihydropinidine and dendrobate alkaloid (+)-241D
    Chenevert, R
    Dickman, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) : 3332 - 3341
  • [3] A practical asymmetric synthesis of 2,6-cis-disubstituted piperidines
    Ciblat, S
    Besse, P
    Canet, JL
    Troin, Y
    Veschambre, H
    Gelas, J
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (11) : 2225 - 2235
  • [4] A simple synthesis of (+)- and (-)-alkaloid 241D and C-4 epimers
    Ciblat, S
    Calinaud, P
    Canet, JL
    Troin, Y
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (03): : 353 - 357
  • [5] Davis FA, 2000, SYNTHESIS-STUTTGART, P2106
  • [6] δ-amino β-keto esters, a designed polyfunctionalized chiral building block for alkaloid synthesis.: Asymmetric synthesis of (R)-(+)-2-phenylpiperidine and (-)-SS20846A
    Davis, FA
    Chao, B
    Fang, TN
    Szewczyk, JM
    [J]. ORGANIC LETTERS, 2000, 2 (08) : 1041 - 1043
  • [7] Alkaloid synthesis using chiral δ-amino β-ketoesters:: A stereoselective synthesis of (-)-lasubine II
    Davis, FA
    Chao, B
    [J]. ORGANIC LETTERS, 2000, 2 (17) : 2623 - 2625
  • [8] Davis FA, 1998, CHEM SOC REV, V27, P13
  • [9] Introduction (Audience research in the theatre)
    Davis, TC
    Mcconachie, B
    [J]. THEATRE SURVEY, 1998, 39 (02) : 1 - 5
  • [10] ALKALOIDS FROM A PANAMANIAN POISON FROG, DENDROBATES-SPECIOSUS - IDENTIFICATION OF PUMILIOTOXIN-A AND ALLOPUMILIOTOXIN CLASS ALKALOIDS, 3,5-DISUBSTITUTED INDOLIZIDINES, 5-SUBSTITUTED 8-METHYLINDOLIZIDINES, AND A 2-METHYL-6-NONYL-4-HYDROXYPIPERIDINE
    EDWARDS, MW
    DALY, JW
    [J]. JOURNAL OF NATURAL PRODUCTS, 1988, 51 (06): : 1188 - 1197