Total synthesis of lycoricidine via photochemical dearomative dihydroxylation

Lycoricidine a member of the amaryllidaceae isocarbostyril alkaloid family of natural products isolated from bulbs of plants in the amaryllidaceae family, which include the common daffodil. The compound has been demonstrated to possess significant biological activity against a wide range of cancer cell lines. As such, lycoricidine, as well other members of the amaryllidaceae isocarbostyril alkaloid family, has been the target of a number of total syntheses by many investigators, which are outlined in detail herein. This thesis documents a novel total synthesis of lycoricidine utilizing a photochemical dearomative dihydroxylation of bromobenzene. Modified Narasaka-Sharpless dihydroxylation generates a product bearing both the electrophile and nucleophile for an unprecedented transpositive Suzuki coupling. Hetero-Diels-Alder cycloaddition is used to form the syn-1,4-amidoalcohol functionality. This new route completes the total synthesis of lycoricidine in eight steps, shorter than any previously completed synthesis.

Name thesis:degree_name

M.S.

Level thesis:degree_level

Thesis

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2017

Author dc:creator

• Holycross, Daniel Robert

Contributors dc:contributor

• Sarlah, David

• Lycoricidine
• total synthesis
• dearomative dihydroxylation

Statement dc:rights

• Copyright 2016 Daniel Holycross

Language dc:language

en

Handle dc:identifier

http://hdl.handle.net/2142/95520

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/95520