SYNTHESIS OF INDOLIZIDINE AND PYRROLIZIDINE ALKALOIDS BY THE [2+2]-CYCLOADDITION OF ENDOCYCLIC ENECARBAMATES TO ALKYL KETENES

被引:0
|
作者
CORREIA, CRD
DEFARIA, AR
CARVALHO, ES
机构
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total syntheses of the necine base (+/-)-platynecine and of a new indolizidine were accomplished. Both syntheses feature a [2+2] cycloaddition of a common endocyclic enecarbamate with alkylketenes in a new and concise strategy for the construction of pyrrolizidine and indolizidine skeleta. These syntheses were carried out in four steps in good overall yields.
引用
收藏
页码:5109 / 5112
页数:4
相关论文
共 50 条
  • [1] Palladium-Catalyzed Synthesis of Endocyclic Allenes and Their Application in Stereoselective [2+2]Cycloaddition with Ketenes
    Ogasawara, Masamichi
    Okada, Atsushi
    Nakajima, Kiyohiko
    Takahashi, Tamotsu
    [J]. ORGANIC LETTERS, 2009, 11 (01) : 177 - 180
  • [2] Synthesis of indolizidines and pyrrolizidines through the [2+2]cycloaddition of five-membered endocyclic enecarbamates to alkyl ketenes. Unusual regioselectivity of Baeyer-Villiger ring expansions of alkyl aza-bicyclic cyclobutanones
    de Faria, AR
    Salvador, EL
    Correia, CRD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11): : 3651 - 3661
  • [3] [2+2] CYCLOADDITION REACTION OF CYCLIC ENECARBAMATES AND ENAMIDES WITH KETENES - A SHORT AND EFFICIENT SYNTHESIS OF THE GEISSMAN-WAISS LACTONE
    DEFARIA, AR
    MATOS, CRR
    CORREIA, CRD
    [J]. TETRAHEDRON LETTERS, 1993, 34 (01) : 27 - 30
  • [4] A new entry to the synthesis of substituted azetidines: [2+2] cycloaddition reaction of four-membered endocyclic enamides to ketenes
    Burtoloso, Antonio Carlos B.
    Correia, Carlos Roque D.
    [J]. TETRAHEDRON LETTERS, 2006, 47 (36) : 6377 - 6380
  • [5] Stereocontrolled Cyclic Nitrone Cycloaddition Strategy for the Synthesis of Pyrrolizidine and Indolizidine Alkaloids
    Brandi, Alberto
    Cardona, Francesca
    Cicchi, Stefano
    Cordero, Franca M.
    Goti, Andrea
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (32) : 7808 - 7821
  • [6] Diastereofacial selectivity in ketene [2+2] cycloaddition to endocyclic enecarbamates bearing a chiral auxiliary. Synthesis of the (-)-Geissman-Waiss lactone
    Miranda, PCML
    Correia, CRD
    [J]. TETRAHEDRON LETTERS, 1999, 40 (44) : 7735 - 7738
  • [7] [2+2] CYCLOADDITION OF OPTICALLY-ACTIVE KETENES - SYNTHESIS OF (-)-BLASTMYCINONE
    FRATER, G
    MULLER, U
    GUNTHER, W
    [J]. HELVETICA CHIMICA ACTA, 1986, 69 (08) : 1858 - 1861
  • [8] Preparation of β-lactams by [2+2] cycloaddition of ketenes and imines
    Fu, Nanyan
    Tidwell, Thomas T.
    [J]. TETRAHEDRON, 2008, 64 (46) : 10465 - 10496
  • [9] [2+2]CYCLOADDITION OF CYCLIC VINYL PHOSPHONATES WITH KETENES
    DING, M
    RUDER, SM
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 392 - ORGN
  • [10] Asymmetric [2+2] cycloaddition of ketenes: Toward the total synthesis of (+)-lactacystin and (-)-salinosporamide A
    Rulliere, Pauline
    Carret, Sebastien
    Poisson, Jean-Francois
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250