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Synthesis of Five Analogues of Sarcophytol A

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Title:Synthesis of Five Analogues of Sarcophytol A
Authors:Oh, Lynette
Contributors:Chemistry (department)
Date Issued:15 Jan 2014
Publisher:University of Hawaii at Manoa
Abstract:The synthesis of five analogs of Sarcophytol A is described. All five compounds are composed of a six membered ring with an alcohol substituent at C-1 and varying substituents at C- 2 and C-4. The 4-phenylcyclohexanol series of compounds begin their synthesis with commercially available 4-phenylcyclohexanone while the 4-isopropylidene cyclohexanol series of compounds is derived from a common synthetic intermediate. This intermediate is efficiently synthesized from commercially available beta-pinene in four steps. The steps include (a) ozonolysis, (b) carbonylation of nopinone, (c) Lewis-acid induced cleavage of the cyclobutane ring and (d) elimination of the tertiary center to generate the requisite isopropylidene moiety at C-4.
Pages/Duration:vi, 30 pages
Rights:All UHM Honors Projects are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission from the copyright owner.
Appears in Collections: Honors Projects for Chemistry

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