The pyridinium reduction route to alkaloids:: a synthesis of (±)-tashiromine

被引:42
作者
Bates, RW
Boonsombat, J
机构
[1] Chulabhorn Res Inst, Bangkok 10210, Thailand
[2] Chulalongkorn Univ, Dept Chem, Bangkok 10330, Thailand
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 07期
关键词
D O I
10.1039/b100407g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An indolizidine natural product, (+/-)-tashiromine, has been synthesized as a single diastereoisomer by a simple protocol. The key steps of the synthesis include a heterogeneous Sonogashira reaction and a stereoelectronically controlled reduction of a bicyclic pyridinium ion.
引用
收藏
页码:654 / 656
页数:3
相关论文
共 24 条
  • [1] Synthesis of substituted piperidines, indolizidines, quinolizidines, and pyrrolizidines via a cycloaddition strategy using acetylenic sulfones as alkene dipole equivalents
    Back, TG
    Nakajima, K
    [J]. ORGANIC LETTERS, 1999, 1 (02) : 261 - 263
  • [2] BATES RW, 2000, ORGANIC SYNTHESIS US, P11
  • [3] THE SYNTHESIS OF INDOLIZIDINE AND QUINOLIZIDINE RING-SYSTEMS BY FREE-RADICAL CYCLIZATION OF 4-AZA-6-METHOXYCARBONYL-5-HEXENYL RADICALS
    BECKWITH, ALJ
    WESTWOOD, SW
    [J]. TETRAHEDRON, 1989, 45 (16) : 5269 - 5282
  • [4] Chiral NADH models in the pyrido[3,2-c]azepin series. Conformational effect of the carbonyl group in the stereocontrol of reductions
    Bedat, J
    Levacher, V
    Dupas, G
    Queguiner, G
    Bourguignon, J
    [J]. CHEMISTRY LETTERS, 1996, (05) : 359 - 360
  • [5] BLEICHER L, 1995, SYNLETT, P1115
  • [6] A unified strategy for the synthesis of phenanthroizidine alkaloids: Preparation of sterically congested pyridines
    Ciufolini, MA
    Roschangar, F
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (48) : 12082 - 12089
  • [7] Enamino ester reduction:: A short enantioselective route to pyrrolizidine and indolizidine alkaloids.: Synthesis of (+)-laburnine, (+)-tashiromine, and (-)-isoretronecanol
    David, O
    Blot, J
    Bellec, C
    Fargeau-Bellassoued, MC
    Haviari, G
    Célérier, JP
    Lhommet, G
    Gramain, JC
    Gardette, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) : 3122 - 3131
  • [8] DESLONGCHAMPS P, 1983, STEREOELECTRONIC EFF, P211
  • [9] Farina V., 1997, ORG REACT, V50, P1, DOI DOI 10.1002/0471264180.or050.01
  • [10] A synthesis of (-)-tashiromine and formal synthesis of (+)-tashiromine utilizing a highly enantioselective pyrrole/cobaloxime pi-cation cyclization
    Gage, JL
    Branchard, BP
    [J]. TETRAHEDRON LETTERS, 1997, 38 (40) : 7007 - 7010