Synthesis of (1R,2R,7R,7aS)-1-hydroxymethyl-2,3,5,6,7,7a-hexahydropyrrolizidine-1,2,7-triol from rosmarinine degradation

被引:0
|
作者
Nieto-Alvarez, DA
Calderón, JS
Mancilla, T
机构
[1] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico
[2] Univ Nacl Autonoma Mexico, Inst Quim, Mexico City 04510, DF, Mexico
关键词
tetrahydroxypyrrolizidine; polyhydroxypyrrolizidine; pyrrolizidine; alkaloids;
D O I
10.1080/1057563021000028000
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A novel tetrahydroxypyrrolizidine alkaloid (6) was obtained from rosmarinine degradation in 23% yield (isolated from Senecio callosus)
引用
收藏
页码:33 / 36
页数:4
相关论文
共 50 条
  • [31] (1R,2R,3R,3′R,4R)-3-[(2-furyl)hydroxymethyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol, a new camphor-based chiral auxiliary
    Branco, MC
    Gambardella, MTD
    Vasconcellos, MLAA
    Barreiros, UG
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1999, 55 : 1295 - 1297
  • [32] A novel and efficient synthesis of (6R,7R)-7-Amino-3-hydroxymethyl cephalosporanic acid: A versatile precursor of cefuroxime acid
    Singh, SK
    Tiwari, RP
    Jain, P
    SYNTHETIC COMMUNICATIONS, 2003, 33 (14) : 2475 - 2482
  • [33] Synthesis of (1R,2R)- and (1S,2R)-1,2-Epoxy-3-hydroxypropylphosphonates as Analogues of Fosfomycin
    Wroblewski, Andrzej E.
    Szewczyk, Eligia M.
    Bak-Sypien, Irena I.
    ARCHIV DER PHARMAZIE, 2009, 342 (09) : 521 - 527
  • [34] Diastereoselective synthesis of polyfunctional-pyrrolidines via vinyl epoxide aminolysis/ring-closing metathesis:: Synthesis of chiral 2,5-dihydropyrroles and (1R,2S,7R,7aR)-1,2,7-trihydroxypyrrolizidine
    Lindsay, KB
    Tang, MY
    Pyne, SG
    SYNLETT, 2002, (05) : 731 - 734
  • [35] Synthesis of diethyl (1R,2R)- and (1S,2R)-3-acetamido-1,2-dihydroxypropylphosphonates
    Wróblewski, AE
    Balcerzak, KB
    TETRAHEDRON-ASYMMETRY, 2002, 13 (08) : 845 - 850
  • [36] Versatile methodology for the synthesis and α-functionalization of (2R,3aS,7aS)-octahydroindole-2-carboxylic acid
    Sayago, Francisco J.
    Calaza, M. Isabel
    Jimenez, Ana I.
    Cativiela, Carlos
    TETRAHEDRON, 2008, 64 (01) : 84 - 91
  • [37] A cocrystal of (2S,3aS,4R,5R,7aS)- and (2R,3aS,4R,5R,7aS)-7-bromo-2-(4-methoxyphenyl)-3a,4,5,7a-tetrahydro-1,3-benzodioxole-4,5-diol (17:3)
    Banwell, Martin G.
    Kokas, Okanya J.
    Willis, Anthony C.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O4187 - U4311
  • [38] A NOVEL STEREOSELECTIVE SYNTHESIS OF THE MACROCYCLE OF HEME D1 THAT ESTABLISHES ITS ABSOLUTE-CONFIGURATION AS 2R,7R
    MICKLEFIELD, J
    MACKMAN, RL
    AUCKEN, CJ
    BECKMANN, M
    BLOCK, MH
    LEEPER, FJ
    BATTERSBY, AR
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (03) : 275 - 277
  • [39] Crystal structure of dimethyl (1R*,2R*,3S*,4R*,6R*7R*9R*,13R*)-2,13-dibromo-6-methoxy-5-oxatetracyclo[7.4.0.01,4.03,7]tridecane-2,3-dicarboxylate, C17H22Br2O6
    Peters, EM
    Peters, K
    Neumann, M
    Tochtermann, W
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2001, 216 (03): : 469 - 470
  • [40] (1R,2R,3R,3 prime R,4R)-3-[(2-Furyl)hydroxymethyl]-1,7,7- trimethylbicyclo[2.2.1]heptan-2-ol, a new camphor-based chiral auxiliary
    Branco, Marcelo Cardoso
    Gambardella, Maria Teresa Do P.
    Vasconcellos, Mario L. A. A.
    Barreiros, Uendel G.
    Acta Crystallographica Section C: Crystal Structure Communications, 1999, 55 (08): : 1295 - 1297