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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
(Massey University, 1987) Gibson, Jennifer Joy
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.