Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 8, Pages 1534-1543Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001527
Keywords
Natural products; Synthetic methods; Epoxidation; Enantioselectivity; Enzymatic resolution; Divergent synthesis
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Funding
- Ministerio de Educacion y Ciencia (MEC) [CTQ2007-60613]
- Direccio General de Recerca
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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: alpha-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.
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