LE3 .A278 2019

2019

Jha, Amitabh

Acadia University

Bachelor of Science

Honours

Chemistry

Chemistry

Polyheterocyclic frameworks, such as steroids, are very important moieties for the construction of biologically and pharmaceutically relevant molecules. However, synthesis of these structurally complex molecules in a short route from readily available starting materials is a challenge in the field of organic chemistry and therefore is being widely investigated. This thesis reports a transition metal-free four-step synthetic pathway to produce tetracyclic heterosteroid compounds, starting from 2-naphthol analogs. After conversion of 2-naphthols to 2-naphtylamines via the Burcherer reaction, subsequent selective C-acetylation via the Sugasawa reaction and reduction of the acetyl group using borohydride, 1-(1-hydroxyethyl)-2-aminonaphthalenes was obtained. These amino-alcohols underwent double dehydrations and double intramolecular cyclisation with oxo-acids in a one-pot formation of a C-N bond, a C-O bond and an amide bond in tandem. In total, six novel 14-aza-12-oxa-steroid analogues were synthesised which were characterised through their 1H and 13 C{1H} NMR spectroscopies and high-resolution mass spectra

The author retains copyright in this thesis. Any substantial copying or any other actions that exceed fair dealing or other exceptions in the Copyright Act require the permission of the author.

https://scholar.acadiau.ca/islandora/object/theses:3257