A convenient C–H functionalization platform for pyrroloiminoquinone alkaloid synthesis

Myles W. Smith, Isaac D. Falk, Hideya Ikemoto, Noah Z. Burns

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

Pyrroloiminoquinone alkaloids represent a structurally intriguing class of natural products that display an array of useful biological properties. Here, we present a versatile and scalable platform for the synthesis of this diverse family – and in particular the antitumor discorhabdins – built upon sequential selective C–H functionalization of tryptamine. The utility of this strategy is showcased through short formal syntheses of damirones A–C, makaluvamines D and I, and discorhadbin E. Additionally, we describe efforts to develop the first catalytic asymmetric entry to the discorhabdin subclass.

Original languageEnglish (US)
Pages (from-to)3366-3370
Number of pages5
JournalTetrahedron
Volume75
Issue number24
DOIs
StatePublished - Jun 14 2019

Keywords

  • Alkaloids
  • C–H functionalization
  • Natural products
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'A convenient C–H functionalization platform for pyrroloiminoquinone alkaloid synthesis'. Together they form a unique fingerprint.

  • Cite this