Development of algorithmically prioritized methods for generalized natural product synthesis

The synthesis of small molecule natural products has long captivated the attention of chemists and has generally proceeded via custom solutions to specific molecules. We propose to instead utilize a human guided algorithm to analyze a building block approach to natural products and identify key methodologies. Additionally, the stereochemical make up around each coupling can be used to help guide the creation of a substrate table. Herein we report the use of an algorithm to systematically fragment all linear natural product, conduct an optimization to choose the smallest set of blocks required to cover >75% of natural product chemical space, and establish a list of impactful couplings. We then selected one of the couplings and used a data driven substrate scope to guide methodological development that covered the predetermined substrates.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2022

Author dc:creator

• Simons, Claire Lillian Wolfe

Contributors dc:contributor

• Burke, Martin D
• van der Donk, Wilfred A
• Mitchell, Douglas A
• Peng, Jian

• Natural product synthesis
• building block synthesis
• computationally guided methodology

Statement dc:rights

• Copyright 2021 Claire Simons

Language dc:language

en

Handle dc:identifier

http://hdl.handle.net/2142/113292

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/113292