Intramolecular hydride transfer has long been recognized as a powerful method to generate new stereogenic centers induced by the existing stereogenic center(s).Synthetically significant selectivities are usually obtained through 1,5-hydride transfer within sixmembered ring.This mini-review focuses on a transannular hydride transfer generating up to three stereocenters simultaneously from a single stereogenic center through formation of medium rings, mostly eight-membered rings, in mild reaction conditions.The corresponding linear products with multiple stereocenters are potentially useful building blocks for synthesis of complex molecules including polyketide natural products.