Rapid access to 6-bromo-5,7-dihydroxyphthalide 5-methyl ether by a CuBr2-mediated multi-step reaction: Concise total syntheses of hericenone J and 5′-deoxohericenone C (hericene A)

Shoji Kobayashi*, Ami Ando, Hiroyuki Kuroda, Shota Ejima, Araki Masuyama, Ilhyong Ryu

*Corresponding author for this work

Research output: Contribution to journalArticle

14 Scopus citations

Abstract

A practical route to 6-bromo-5,7-dihydroxyphthalide 5-methyl ether, a versatile intermediate in the synthesis of hericenones and related bioactive polyphenols, was developed. The synthesis features a combination of tandem Michael addition-Claisen condensation and CuBr2-mediated multi-step reactions. With this product in hand, total syntheses of hericenone J and 5′-deoxohericenone C (hericene A) were achieved.

Original languageEnglish
Pages (from-to)9087-9092
Number of pages6
JournalTetrahedron
Volume67
Issue number47
DOIs
StatePublished - 25 Nov 2011

Keywords

  • Copper(II) bromide (CuBr )
  • Hericene
  • Hericenone
  • Multi-step reaction
  • Stille coupling

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