Ring-closing metathesis and palladium-catalyzed formate reduction to 3-methyleneoxepanes. Formal synthesis of (-)-zoapatanol

Hsiu Yi Cheng, Yu Shiang Lin, Chong Si Sun, Ting Wen Shih, Hui Hsu Gavin Tsai, Duen Ren Hou

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

A sequence of ring-closing metathesis and palladium-catalyzed formate reduction was developed for preparing O-heterocycles with an exocyclic olefin and applied to the asymmetric synthesis of zoapatanol. The key vicinal stereocenters in zoapatanol were constructed from the l-malic acid-derived lactone by successive chelation-controlled addition of alkyl groups. The O-allylations to prepare the dienes for RCM were achieved with the tertiary alcohols bearing internal olefins. The ring opening of oxepane, a new reaction pathway for the Pd-formate reduction, is also reported.

Original languageEnglish
Pages (from-to)747-753
Number of pages7
JournalTetrahedron
Volume68
Issue number2
DOIs
StatePublished - 14 Jan 2012

Keywords

  • Exocyclic olefin
  • Metathesis
  • Palladium-formate reduction
  • Zoapatanol

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