Browsing by Author "Wisch, Gregory A"

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    The X-ray crystal structures of ambraketal and 8-epi-ambraketal
    (Science Reviews 2000 Ltd, 2003) Gray, Christopher A; Davies-Coleman, Michael T; Caira, Mino R; Nathansona, Carole A; Wisch, Gregory A
    The crystal structures of ambraketal and 8-epi-ambraketal, synthesised in five steps from (–)-sclareol, are reported. Ambergris, a concretion formed in the intestinal tract of the blue sperm whale, has been used by perfumers since ancient times because of its unique fragrance and fixative properties.1 Restrictions imposed upon the whaling industry, in an attempt to protect these endangered marine mammals, have forced chemists to make synthetic substitutes for ambergris. Among these synthetic substitutes, the two epimeric bisnorlabdane acetals ambraketal (1; amberketal, ambracetal) and 8-epiambraketal (2, epi-amberketal, 8-epi-ambracetal, isoambraketal) have found prominence due to their strong fragrance and fixative properties respectively. Compounds 1 and 2 have also been reported as minor constituents in the bark of the western white pine tree (Pinus monticola).2