Files in this item

FilesDescriptionFormat

application/pdf

application/pdfHOLYCROSS-THESIS-2016.pdf (6MB)Restricted to U of Illinois
(no description provided)PDF

Description

Title:Total synthesis of lycoricidine via photochemical dearomative dihydroxylation
Author(s):Holycross, Daniel Robert
Advisor(s):Sarlah, David
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:M.S.
Genre:Thesis
Subject(s):Lycoricidine
total synthesis
dearomative dihydroxylation
Abstract: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.
Issue Date:2016-12-08
Type:Thesis
URI:http://hdl.handle.net/2142/95520
Rights Information:Copyright 2016 Daniel Holycross
Date Available in IDEALS:2017-03-01
Date Deposited:2016-12


This item appears in the following Collection(s)

Item Statistics