(±)-4-Epi-helminthosporal, (2), is synthesised from geranyl chloride and 3-methoxy-1-phenylthiopropyne, by a five stage sequence in which the key step, leading to the bicyclo[3.2.1]oct-6-ene skeleton, is a zinc chloride catalysed [3 + 2]cycloaddition of an allyl cation to an alkyne.
B. D. Gray and J. A. Miller, J. Chem. Soc., Chem. Commun., 1987, 1136 DOI: 10.1039/C39870001136
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