The Alstoscholarisine Alkaloids: Isolation, Structure Determination, Biogenesis, Biological Evaluation, and Synthesis

Jeremy D. Mason, Steven M. Weinreb

Research output: Chapter in Book/Report/Conference proceedingChapter

9 Scopus citations

Abstract

The alstoscholarisines are a small family of biologically and structurally interesting polycyclic monoterpenoid indole alkaloids isolated from the leaf extracts of Alstonia scholaris. The alkaloids can be divided into three different subtypes based upon their structures and putative biogenesis: (1) (−)-alstoscholarisines A–E, (2) (+)-alstoscholarisine G, and (3) (+)-alstoscholarisines H–J. This review discusses the isolation, structure determination, biological activity, and proposed biosynthesis of these metabolites. In addition, synthetic studies on the alkaloids are described including total syntheses of racemic alstoscholarisines A–E, a total synthesis of (−)-alstoscholarisine A, and a synthesis of racemic alstoscholarisine H.

Original languageEnglish (US)
Title of host publicationAlkaloids
Subtitle of host publicationChemistry and Biology
EditorsHans-Joachim Knölker
PublisherAcademic Press Inc.
Pages115-150
Number of pages36
ISBN (Print)9780128171516
DOIs
StatePublished - 2019

Publication series

NameAlkaloids: Chemistry and Biology
Volume81
ISSN (Print)1099-4831

All Science Journal Classification (ASJC) codes

  • Biochemistry

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