Total synthesis of JBIR-03 and asporyzin C

Tetsuro Murokawa, Masaru Enomoto, Takaaki Teranishi, Yusuke Ogura, Shigefumi Kuwahara

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

The first enantioselective total synthesis of JBIR-03 and asporyzin C, indole diterpenoids of fungal origin exhibiting a range of pharmacologically important biological activities, has been accomplished from a known bicyclic keto alcohol in 13 and 14 steps, respectively. A hydroxy-directed cyclopropanation and Pd(II)-mediated indole ring formation were exploited as the key steps to obtain a pivotal pentacylic intermediate, which was converted into asporyzin C via chain elongation using cross-metathesis and then into JBIR-03 by Pd(II)-catalyzed tetrahydrofuran ring formation in an exclusively diastereoselective manner.

Original languageEnglish
Pages (from-to)4107-4109
Number of pages3
JournalTetrahedron Letters
Volume59
Issue number46
DOIs
Publication statusPublished - 2018 Nov 14

Keywords

  • Asporyzin
  • Indole diterpenoid
  • JBIR-03
  • Palladium catalysis
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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