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ISHS Acta Horticulturae 464: International Postharvest Science Conference Postharvest 96

THE PREPARATION OF α-FARNESENE HYDROPEROXIDES FOR THE STUDY OF SUPERFICIAL SCALD

Authors:   S. Fielder, M. S. Sherburn, Daryl D. Rowan
DOI:   10.17660/ActaHortic.1998.464.24
Abstract:
The short and efficient synthesis of four alpha-farnesene autoxidation products is described. Geraniol was converted to the conjugated trienyl hydroperoxide (3) via the known trienol (2). Trienyl hydroperoxide (3) was efficiently cyclised in the presence of oxygen and an intiator to afford the very labile endoperoxy hydroperoxide (5), a route which mimics alpha-farnesene autoxidation. Reduction of (5) gave the endoperoxy alcohol (4).


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