A concise total synthesis of (+)-scholarisine a empowered by a unique C-H arylation

Myles W. Smith, Scott A. Snyder

Research output: Contribution to journalArticle

95 Scopus citations

Abstract

The structurally unique akuammiline alkaloid (+)-scholarisine A was synthesized in 14 steps from a known enone (15 steps from commercial materials) through a route empowered by a unique C-H arylation reaction to forge its polycyclic core. Additional key steps include a pyrone Diels-Alder reaction and a radical cyclization/Keck allylation to fashion the core cage polycycle and one of the molecule's quaternary centers, as well as the use of a carefully positioned pendant hydroxyl group to facilitate the chemoselective reduction of an extremely unreactive lactam in the presence of a readily reduced lactone.

Original languageEnglish (US)
Pages (from-to)12964-12967
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number35
DOIs
StatePublished - Sep 4 2013
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'A concise total synthesis of (+)-scholarisine a empowered by a unique C-H arylation'. Together they form a unique fingerprint.

  • Cite this