SYNTHESIS OF INDOLIZINOQUINOLINONES THROUGH THREE- AND FOUR-COMPONENT DOMINO KNOEVENAGEL / HETERO-DIELS–ALDER REACTIONS: NOVEL ACCESS TO (+)-CAMPTOTHECIN

Авторы

  • Lutz F. Tietze Institute of Organic and Biomolelecular Chemistry Georg-August University Göttingen
  • Matthias Bischoff
  • Taukeer A. Khan
  • Deshan Liu deceased

DOI:

https://doi.org/10.1007/3649

Ключевые слова:

alkaloids, camptothecin, indolizinoquinolinones, domino reactions, hetero-Diels–Alder reaction, natural product synthesis, oxidation

Аннотация

The fused heterocyclic indolizinoquinolinone system is a key structural feature of several highly bioactive alkaloids, including campto-thecin. Camptothecin has been efficiently obtained by a three- or four-component domino Knoevenagel / hetero-Diels–Alder reaction of aldehyde, Meldrum's acid, and enol ether in the presence or absence of alcohol, followed by reductive cleavage of the amine protecting group. The obtained products were further transformed along several different routes leading to camptothecin.

 

Загрузки

Опубликован

2017-05-11

Выпуск

Том 53 № 4 (2017): Многокомпонентные реакции в синтезе гетероциклов

Раздел

Оригинальные статьи