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oai:www.ideals.illinois.edu:2142/84434 2023-07-11 col_2142_5131 col_2142_14789 com_2142_5130 com_2142_14788 com_2142_8903

Coates, Robert M. Duffy, Bryan C. 2015-09-25T22:14:29Z 2015-09-25T22:14:29Z 10000-01-01 1999 1999 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. Made available in DSpace on 2015-09-25T22:14:29Z (GMT). No. of bitstreams: 2 license.txt: 4848 bytes, checksum: 96035ab3f5e1c23cc7138a224ce498bd (MD5) 9921683.pdf: 10035729 bytes, checksum: ec6dae4d160bde05c4ed25faf1045686 (MD5) Previous issue date: 1999 Embargo set by: Seth Robbins for item 85715 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs U of I Only 242 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1999. http://hdl.handle.net/2142/84434 (MiAaPQ)AAI9921683 eng Chemistry, Organic The Synthesis of (+/-)-Presilphiperfol-7(8)-Ene and Tertiary Tricyclo(5.3.1.0(4,11))undecanols Related to Presilphiperfolan-8-Ol text Chemistry Chemistry University of Illinois at Urbana-Champaign Dissertation Ph.D.