Divergent approach to gabosines and anhydrogabosines: Enantioselective syntheses of (+)-epiepoformin, (+)-EpoKformin, (+)-gabosine A, and gabosines B and F

Gladis Toribio, Georgina Marjanet, Ramon Alibés, Pedro De March, Josep Font, Pau Bayón, Marta Figueredo

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27 Citations (Scopus)

Abstract

A divergent approach to polyoxygenated methylcyclohexanes has been applied to synthesize several gabosines and anhydrogabosines. The starting hydroxycyclohexenone, which is readily available in any antipodal form, provides access to both enantiomers of the target compounds. The syntheses of anhydrogabosines involve three main transformations: α-methylation, epoxidation, and sulfur removal, whereas the syntheses of gabosines require an additional epoxide hydrolysis step. The strategy has been applied to the synthesis of (+)-epiepoformin, (+)-epoformin, (+)-gabosine A, and gabosines B and F, through straightforward sequences in good overall yields. A cyclohexenone that is easily available in any antipodal form has been used as the starting material to synthesize various gabosines and anhydrogabosines through a divergent strategy. The syntheses of anhydrogabosines involve three main transformations: α-methylation, epoxidation, and sulfur removal, whereas the syntheses of gabosines require an additional epoxide hydrolysis step. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Original languageEnglish
Pages (from-to)1534-1543
JournalEuropean Journal of Organic Chemistry
Issue number8
DOIs
Publication statusPublished - 1 Mar 2011

Keywords

  • Divergent synthesis
  • Enantioselectivity
  • Enzymatic resolution
  • Epoxidation
  • Natural products
  • Synthetic methods

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