Abietic acid in the synthesis of unnatural alkaloids
Files
Honors Thesis
Date
2014-04
DOI
Authors
Gale-Day, Zachary John
Version
OA Version
Citation
Abstract
The synthesis of unnatural alkaloid-type products from abietic acid was explored. In order to synthesize these products the protection of the carboxylic acid was achieved followed by a selective dihydroxylation of the C-ring was followed by oxidative diol cleavage. Using the dione yielded a reductive aminocyclization followed. This reaction was first explored using 4-methoxybenzylamine and after optimization the alkaloid-type product was synthesized in a 34% yield. Using the optimized conditions a small library of analogues were synthesized utilizing different primary amines.
Description
Honors Thesis, BA in Chemistry 2014
License
CC0 1.0 Universal