Isolation of (+)-fusicocca-2,10(14)-diene, a 5-8-5 tricyclic diterpene hydrocarbon biosynthetically related to the fusicoccin aglycon from Fusicoccum amygdali and confirmation of its structure by total synthesis

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Nobuo Kato, Chang-Shan Zhang, Takayuki Matsui, Hisakatsu Iwabuchi, Akira Mori, Alessandro Ballio and Takeshi Sassa


Abstract

(+)-Fusicocca-2,10(14)-diene, a double bond isomer of the putative fusicoccin biosynthetic intermediate, i.e., fusicocca-1,10(14)-diene, was isolated for the first time as a main hydrocarbon constituent from the fusicoccin-producing fungus Fusicoccum amygdali, and its stereostructure including absolute configuration was unambiguously confirmed by total synthesis.


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