The cyclisation of 1,5-enynes containing alkenes, arenes, heteroarenes, and hydroxyl groups to form polycyclic compounds has been achieved with a cationic dicyclohexylphosphinobiphenyl gold(I) complex as catalyst under mild conditions and with low catalyst loadings. The polycyclisation has been extended to the simultaneous formation of up to four carbon-carbon bonds in bioinspired transformations.