A reliable strategy for the construction of trans-fused bicyclo[n.3.0] skeletons was explored by utilizing photoinduced cyclization of acylsilanes bearing a boronate. The substrates having an acylsilane and a boronate in a 1,2-trans relationship were prepared via hydroboration of cycloalkene derivatives. The desired cyclization was efficiently promoted by photoirradiation to give the trans-fused bicyclo[n.3.0] derivatives as a single diastereomer. It is noteworthy that this methodology enables the efficient construction of a highly strained trans-5-5 ring system.