Synthesis of (±)-pterosin A via Suzuki-Miyaura cross-coupling reaction

Shao Chien Hsu, Mogili Narsingam, Yi Fang Lin, Feng Lin Hsu, Biing Jiun Uang

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

A practical synthesis of (±)-pterosin A from commercially available 2-bromo-1,3-dimethyl-benzene 5 has been accomplished in 10% overall yield. The synthesis used Suzuki-Miyaura coupling reaction of C6-bromoindanone derivative 3 with potassium vinyltrifluoroborate 9, which provided the corresponding vinylindanone 2 in >85% yield. The vinylindanone 2 could be further elaborated to pterosin A by reduction with LAH, selective protection of primary alcohol with TESCl, hydroboration-oxidation of vinyl group, protection of primary alcohol with TIPSCl, oxidation of the secondary alcohol, and desilylation with TBAF.

Original languageEnglish
Pages (from-to)2572-2576
Number of pages5
JournalTetrahedron
Volume69
Issue number12
DOIs
Publication statusPublished - Mar 25 2013

Keywords

  • Potassium vinyltrifluoroborate
  • Pterosin A
  • Suzuki-Miyaura reaction
  • Vinylation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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