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


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.


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.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:Total Synthesis; Methodology; Diterpenoid Alkaloids; Lupin Alkaloids; Myrsinane Diterpenes
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Reisman, Sarah E.
Thesis Committee:
  • Stoltz, Brian M. (chair)
  • Agapie, Theodor
  • Nelson, Hosea M.
  • Reisman, Sarah E.
Defense Date:31 May 2023
Non-Caltech Author Email:jeff_kerkovius (AT)
Funding AgencyGrant Number
Natural Sciences and Engineering Research Council of Canada (NSERC)PGSD3-532535-2019
Resnick Sustainability InstituteUNSPECIFIED
Record Number:CaltechTHESIS:06012023-171716967
Persistent URL:
Related URLs:
URLURL TypeDescription adapted for Ch. 1 adapted for Ch. 2 adapted for Ch. 3
Kerkovius, Jeffrey Kevan0000-0001-5692-0285
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:15258
Deposited By: Jeffrey Kerkovius
Deposited On:09 Jun 2023 15:17
Last Modified:03 May 2024 00:30

Thesis Files

[img] PDF (Redacted thesis, ch. 4 excluded) - Final Version
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