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Title:The Synthesis of (+/-)-Presilphiperfol-7(8)-Ene and Tertiary Tricyclo(5.3.1.0(4,11))undecanols Related to Presilphiperfolan-8-Ol
Author(s):Duffy, Bryan C.
Doctoral Committee Chair(s):Coates, Robert M.
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
Abstract:Functionalization reactions of the double bond of 15-nor-PSP-7(8)-ene were carried out to investigate the possible synthesis of (+/-)-PSP-8-OH from (+/-)-PSP-7(8)-ene. Epoxidation of the double bond with an aqueous buffered m-chloroperbenzoic acid furnished a 2.5:1 mixture of the 7beta,8beta- and 7beta,8beta-epoxides. m-Chlorobenzoic acid catalyzed a facile rearrangement of the 7beta,8beta-epoxide to 15- nor-cameroon-7-one was investigated. Reaction of nor-PSP-7(8)-ene with osmium tetroxide afforded nor-presilphiperfolan-7a,8a-diol, which underwent pinacol rearrangement to 8,10,10-trimethyltricyclo[6.2.1.01,5]undecan-11-one. The same ketone was formed directly by reaction of nor-PSP-7(8)-ene with chromyl chloride. The mechanistic pathways and stereochemical implications of these rearrangements are discussed in detail.
Issue Date:1999
Type:Text
Language:English
Description:242 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1999.
URI:http://hdl.handle.net/2142/84434
Other Identifier(s):(MiAaPQ)AAI9921683
Date Available in IDEALS:2015-09-25
Date Deposited:1999


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