Total Synthesis of Lupin Alkaloids, Diterpenoid Alkaloids, and Progress Towards the Myrsinane Diterpenes

Citation

Kerkovius, Jeffrey Kevan (2023) Total Synthesis of Lupin Alkaloids, Diterpenoid Alkaloids, and Progress Towards the Myrsinane Diterpenes. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/y6rd-nm97. https://resolver.caltech.edu/CaltechTHESIS:06012023-171716967

Abstract

The interplay between total synthesis and methodology is a driver of innovation in organic synthesis. Challenging bond formations in complex systems necessitate the development ever more robust new reactions, which intern can enable more efficient syntheses. The need for powerful synthetic organic chemistry can’t be understated because of its utility in applications such as medicine, petrochemicals, plastics, and agrichemicals.

Herein, we present how total synthesis drives innovation in organic chemistry. First, a novel cyclization reaction between pyridine and glutaryl chloride is discussed, which has enabled the synthesis of seven lupin alkaloids. Next, the development of a convergent fragment coupling tactic based upon the semi-pinacol rearrangement is evaluated for its generality inspired by the total synthesis of several C19 diterpenoid alkaloids. Lastly, a convergent fragment coupling approach is applied to the total synthesis of falcatin A based upon a Mukaiyama Michael tandem Mukaiyama aldol reaction.

Thesis Files