Journal of the Chemical Society. Perkin transactions I p. 1725 - 1730 (1985)
Update date:2022-08-03
Topics:
Bromidge, Steven M.
Sammes, Peter G.
Street, Leslie J.
A route to the sesquiterpene (+/-)-β-bulnesene is described which starts with the substituted furan, 2-(1-hydroxy-4-methylhex-5-enyl)furan.Oxidation of the latter generates a precusor of a 2-substituted 3-oxidopyrylium, which undergoes smooth intramolecular cyclisation to generate a highly functionalised perhydroazulene intermediate.Further chemical manipulation of the latter readily generates the desired natural product.In order to control the relative geometry of the pendent-4-methyl group in the target molecule, a method involving the stereoselective reduction of an exocyclic methylene group is employed; the means for introducing such methylene groups are detailed.
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