Synthetic studies towards panacene : a thesis presented in partial fulfilment of the requirements for the degree of Master of Science in Chemistry at Massey University
dc.contributor.author | Gibson, Jennifer Joy | |
dc.date.accessioned | 2019-02-13T01:19:57Z | |
dc.date.available | 2019-02-13T01:19:57Z | |
dc.date.issued | 1987 | |
dc.description.abstract | SYNTHETIC STUDIES TOWARDS PANACENE (1) 2-Trimethylsilyloxyfuran (l}) and 2-acetyl-1 ,4-benzoquinone (6) were prepared according to published methods. The uncatalysed addition of 2-trfmethylsilyloxyfuran (23) to the quinone (6) gave cis-3a,8b-dihydro-8-acetyl-7-hydroxyfuro [3,2-b]benzofuran-2-(3H)-one (24) in 50% yield. The reaction of other 1,4-benzoquinones was investigated, establishing the necessity of an activating substituent at C-2 of the quinone. Attempts to reduce the acetyl group of cis-3a,8b-dihydro-8- -acetyl-7-hydroxyfuro[3,2-b]benzofuran-2-(3H)-one (24) to the ethyl group present in Panacene (l) were unsuccessful, although reduction of the ketone with sodium borohydride gave cis-3a,8b-dihydro-8-(1 '-hydroxyethyl)-7-hydroxyfuro[3,2-b] benzofuran-2-(3H)-one (51). The conversion of cis-3a,8b-dihydro-8-acetyl-7-hydroxyfuro [3,2-b]henzofuran-2-(3H)-one (24) to cis-3,3a,9b-trihydro- 5-hydroxy-5-methylfuro[3,2-c][2]benzopyran-2,6,9-(5H)-trione (58) was carried out using cerie ammonium nitrate. | en_US |
dc.identifier.uri | http://hdl.handle.net/10179/14251 | |
dc.language.iso | en | en_US |
dc.publisher | Massey University | en_US |
dc.rights | The Author | en_US |
dc.subject | Organic compounds | en_US |
dc.subject | Synthesis | en_US |
dc.subject | Organohalogen compounds | en_US |
dc.subject | Panacene | en_US |
dc.title | Synthetic studies towards panacene : a thesis presented in partial fulfilment of the requirements for the degree of Master of Science in Chemistry at Massey University | en_US |
dc.type | Thesis | en_US |
massey.contributor.author | Gibson, Jennifer Joy | |
thesis.degree.discipline | Chemistry | en_US |
thesis.degree.grantor | Massey University | en_US |
thesis.degree.level | Masters | en_US |
thesis.degree.name | Master of Science (M. Sc.) | en_US |
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