☆ 4.4 Article

Synthesis of D-arabinose-derived polyhydroxylated pyrrolidine, indolizidine and pyrrolizidine alkaloids. Total synthesis of hyacinthacine A2

TETRAHEDRON (2010)

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Journal

TETRAHEDRON
Volume 66, Issue 6, Pages 1220-1227

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.12.030

Keywords

Alkaloids; Pyrrolidines; Nitrones

Categories

Chemistry, Organic

Funding

  1. Spanish Ministry of Science and Education (MEC Madrid, Spain) [CTQ2007-67532-C02-01]
  2. FEDER Program
  3. Government of Aragon
  4. MiUR (Italy)
  5. Gobjerno de Aragon
  6. Spanish Ministry of Science and Education (MEC Madrid, Spain) [CTQ2007-67532-C02-01]
  7. FEDER Program
  8. Government of Aragon
  9. MiUR (Italy)
  10. Gobjerno de Aragon

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Several new polyhydroxylated alkaloids including pyrrolidines with a long side chain and 3-(hydroxymethyl) indolizidines were prepared from a common nitrone easily obtained from Do-arabinose In addition. a total synthesis of hyacinthacine A(2) has been achieved in five steps and 67 7% overall yield starting from the same D-arabino-derived nitrone All synthesized compounds have a common structural feature consisting of a pyrrolidine ring with D-arabino configuration (C) 2009 Elsevier Ltd All rights reserved

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