Enantioselective total synthesis of pinnaic acid and halichlorine

Shu Xu, Daisuke Unabara, Daisuke Uemura, Hirokazu Arimoto

Research output: Contribution to journalArticlepeer-review

33 Citations (Scopus)

Abstract

The enantioselective total synthesis of the bioactive marine natural products pinnaic acid and halichlorine is reported in detail. Our total synthesis features the construction of the five-membered ring and C9 and C13 stereogenic centers through a palladium-catalyzed trimethylenemethane [3+2] cyclization; the installation of the nitrogen atom through a regioselective Beckmann rearrangement of a poorly reactive ketone; the stereoselective cyclization of the spiro ring through a four-step, one-pot hydrogenation- cyclization; and efficient connection of the sterically hindered lower chain through a reduced-pressure cross olefin metathesis reaction.

Original languageEnglish
Pages (from-to)367-375
Number of pages9
JournalChemistry - An Asian Journal
Volume9
Issue number1
DOIs
Publication statusPublished - 2014 Jan

Keywords

  • cyclization
  • metathesis
  • natural products
  • stereoselectivity
  • total synthesis

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