Abstract This work describes the efficient synthesis of functionalized cleft molecules 6, 6a, 16, 16a, 17, 19 and 20 derived from benzopyrano [4, 3-d][1, 3] benzooxazocin-13-one. X-ray crystal structure analysis of compounds 6a and 16a revealed that the cleft angles of the planes of the benzopyran moiety and the p-methoxybenzene ring are 109.4 and 108.6, respectively. The conformation of the aromatic ring at the bridgehead of 16, 16a and 20 is ...