Jiangrine-like scaffolds from biorenewable platforms

Rory Devlin, Shinji Kudo, Jonathan Sperry

Research output: Contribution to journalArticlepeer-review

Abstract

Dihydrolevoglucosenone (DLGO) and amino aldehydes undergo an aldol reaction mediated by the heterogenous base KF-alumina; exposure of the aldol adducts to hydrogenation followed by silica gel results in the formation of pyrrole-2-carbaldehydes bearing the jiangrine alkaloid scaffold. KF-alumina is also an effective base in the aldol condensation between DLGO and aliphatic/aromatic aldehydes, with no self-aldol reaction apparent.

Original languageEnglish
Article number152538
JournalTetrahedron Letters
Volume61
Issue number47
DOIs
Publication statusPublished - Nov 19 2020

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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