Synthesis of novel naphthalene-based 14-AZA-12-oxasteriod analogues
LE3 .A278 2020
2020
Jha, Amitabh
Acadia University
Bachelor of Science
Honours
Chemistry
Steroids have interesting and complex biological functions in humans. Recently, synthesis of heterosteroids have generated great attention because of their interesting biological and pharmacological activities. Therefore, synthesis of heterosteroids molecules is of interest to synthetic chemistsin this study. A transition-metal-free 3-step synthetic pathway to produce a heterosteroid was utilized. This pathway involves a cascade reaction of 1-(1-hydroxyalkyl)-2-aminonaphthalenes with levulinic acid for a tandem C-N and C-O bond formation to lead the synthesis of an amide. ESI-HRMS was conducted on several intermediate and final compounds to determine their exact masses. In total, 6 novel 14-aza-12-oxasteroid analogues were synthesized and were characterized by 1H and 13C{1H} NMR spectroscopies. X-ray crystallography was used to determine the structure of one of the final products.
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https://scholar.acadiau.ca/islandora/object/theses:3381