Colchicine, which is one of the most prominent tubulin-destabilizing agents ever discovered, is well known for its remarkable antimitotic activity. Although numerous strategies have been developed for the construction of the synthetically challenging ring system of colchicine, these processes are largely inefficient, making it difficult to access large enough quantities of these compounds for drug discovery.~1 Here we describe the first highly enantioselective(≥99% ee) and highly concise gram-scale synthesis of(–)-colchicine from commercially available and inexpensive 2,3,4-trimethoxybenzaldehyde in eight steps and an overall yield of 9.0% without any protecting groups. Moreover, the first total synthesis of(+)-demecolcinone, metacolchicine and b-lumicolchicine has also been achieved. Notably, the challenging tricyclic 6-7-7 core of colchicine was efficiently introduced using an intramolecular oxidopyrylium-mediated [5+2] cycloaddition reaction.~2 This work represents the most efficient synthesis of colchicine reported to date with the highest enantioselectivity.