Filling Some Blanks in a Divergent Approach to Gabosines: Enantioselective Synthesis of (–)-Epiepoxydon, (+)-Phyllostine, (–)-Gabosine D, and (–)-Gabosine E

Miguel Ángel Fresneda, Ramon Alibés, Pau Bayón, Marta Figueredo

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9 Citations (Scopus)

Abstract

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim The levorotatory enantiomers of gabosines D and E were synthesized through a divergent approach that could equally well be applied to the synthesis of the dextrorotatory enantiomers, which have been isolated from natural sources. The approach relies on an initial desymmetrization of p-methoxyphenol, followed by an enzymatic resolution that separately provides the two enantiomers of synthon 3. This versatile synthon can be further transformed into the diverse polyoxygenated cyclohexane target molecules. Key steps in the synthesis of (–)-gabosines D and E from (4R,6S)-3 are the stereoselective hydroxymethylation at the α-carbonyl position leading to (+)-4, and the subsequent reagent-controlled epoxidation of the carbon–carbon double bond. A branching in the sequence also allowed the synthesis of the anhydrogabosines (–)-epiepoxydon and (+)-phyllostine.
Original languageEnglish
Pages (from-to)3568-3574
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number21
DOIs
Publication statusPublished - 1 Jan 2016

Keywords

  • Cyclitols
  • Divergent synthesis
  • Eantioselectivity
  • Gabosines
  • Natural products

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