Syntheses of pterocarpenes and coumestans via regioselective cyclodehydration

Maloy Nayak, Youngeun Jung, Ikyon Kim

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13 Citations (Scopus)

Abstract

A highly efficient synthetic route to pterocarpenes and coumestans is described. BCl3-mediated dehydrative cyclization of 1,3-diaryloxyacetones under mild conditions permitted regioselective ring closure to afford 3-((2-iodoaryloxy)methyl)benzofurans which were converted to the corresponding pterocarpenes by Pd-catalyzed intramolecular direct arylation. The subsequent benzylic oxidation led to coumestans. This sequence was applied to the formal syntheses of coumestrol and the proposed structure of plicadin as well as total syntheses of flemichapparins B and C.

Original languageEnglish
Pages (from-to)8074-8087
Number of pages14
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number34
DOIs
Publication statusPublished - 2016 Jan 1

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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