I) ENANTIOSELECTIVE CONJUGATE ADDITION OF ALKENYLBORONIC ACIDS TO INDOLE-APPENDED ENONES II) SYNTHETIC DEVELOPMENTS TOWARD THE APLYKURODIN FAMILY
Lundy, Brian J.
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This dissertation presents two different projects, the first being the use of boronic acids in conjugate addition reactions on different substituted indoles, and the second discusses the strategies toward the synthesis of the natural product, aplykurodinone 1. Conjugate addition reactions are very valuable reactions in forming carbon-carbon bonds and have been studied quite a bit over the years. However, the use of conjugate addition reactions have not been shown to be plausible with unprotected indoles enantioselectively. The previous methods used to do these types of reactions on indoles suffer from limited scope and also require protecting the indole nitrogen. What will be discussed is a very general reaction that tolerates different functional groups such as electron donating and electron withdrawing, as well as tolerating unprotected indoles making it a very useful and powerful method for organic synthesis. The second project I will discuss is efforts toward the total synthesis of the natural product aplykurodinone 1. Aplykurodinone 1 is part of the aplykurodin family of natural products that was found to have potential cytotoxic activity against cancer cell lines. This potential biological activity combined with the interesting steroidal type structure of the natural product piqued our interest and desire to focus efforts to make it synthetically.