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Exploitation of chemical predisposition in synthesis: an approach to the manzamenones

Authors
Journal
Journal of the Chemical Society Perkin Transactions 1
1472-7781
Publisher
The Royal Society of Chemistry
Publication Date
Keywords
  • Diels-Alder Reaction (Dimerization
  • Exploitation Of Chem
  • Predisposition In A Synthetic Approach To The Manzamenones)
  • Dehydration Reaction
  • Stereoselective Synthesis (Exploitation Of Chem
  • Predisposition In A Synthetic Approach To The Manzamenones)
  • Conformation (Mol
  • Modeling
  • Of Manzamenone Analogs)
  • Crystal Structure (Relative Stereostructure From
  • Of Manzamenone Analogs)
  • Dieckmann Condensation (Retro-
  • Exploitation Of Chem
  • Predisposition In A Synthetic Approach To The Manzamenones)
  • Molecular Structure (Revision
  • Relative Stereostructure
  • Of Manzamenones)
  • Natural Products Role: Prp (Properties)
  • Spn (Synthetic Preparation)
  • Prep (Preparation) (Tetrahydroindenone
  • Exploitation Of Chem
  • Predisposition In A Synthetic Approach To The Manzamenones)

Abstract

Full details of the syntheses of manzamenones A (I; R = OH), C (I; R = OEt) and F (I; R = OBu) are reported, using an approach modelled on a plausible biogenetic theory. The key step of the approach is a \"one-pot\" conversion of the antileukemic cyclopentenone, untenone A (II), to manzamenone A (I; R = OH) which occurs in reasonable yield and which proceeds via a reaction sequence of dehydration, Diels-Alder dimerization and retro-Dieckmann reaction. The synthetic approach has also been applied to the prepn. of a no. of shorter alkyl chain analogs of the natural products. Using a combination of NMR and X-ray crystallog. data for the shorter alkyl chain analogs of manzamenone A (I; R = OH), it is suggested that the relative stereostructures of the majority of the manzamenones should be revised such that the acyl group at the C2 position lies on the .alpha.-face and that at the C5 position resides on the .beta.-face. [on SciFinder (R)]

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