A Streamlined Asymmetric Synthesis of SubstitutedGeissman-Waiss Lactones, Oseltamivir Precursors andPeptidyl Hydroxylactams from (–)-Azidocyclohexenol

VOLUME 71 : 2023

A Streamlined Asymmetric Synthesis of SubstitutedGeissman-Waiss Lactones, Oseltamivir Precursors andPeptidyl Hydroxylactams from (–)-Azidocyclohexenol

PAGE 110-118

online publication date: November 2023

Nur Shahidah Sharoman, Gabriel Luis L. Neri, Najmah P. S. Hasan,  Allan Patrick G. Macabeo*, and Mohd Tajudin Mohd Ali* 

ARTICLE DOI: https://doi.org/10.53603/actamanil.71.2023.asfn0398

The asymmetric synthesis of methyl or pentyloxy N,O-bicyclic γ-butyrolactone lactams, 6-aminocyclohex 3-ene-1,2-diol (an oseltamivir precursor) and β-hydroxy lactam tripeptide, starting from (–)-(1S,2S)-1- azido-2-hydroxycyclohexene is hereby described. Synthetic transformations in the developed protocols  include a linear relay of reduction/protection of the azide, allylic hydroxylation, alcoholysis, oxidative  cleavage promoting lactonization/lactamization sequences and methylation. This route provides a simple  synthetic pathway towards necine alkaloid derivatives, the antiviral drug oseltamivir (Tamiflu) and  peptides incorporating rigid lactam units for foldamer synthesis thus extending the usefulness of our  previously reported asymmetric synthetic methodology. 


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