Herein, we report the first asymmetric total synthesis of 4-hydroxy-8-O-methyltetrangomycin (1), 4-hydroxytetrangomycin (2), and 4-keto-8-O-methyltetrangomycin (3), angucyclinones featuring a highly oxidized nonaromatic A ring. A sequential enyne metathesis/Diels-Alder approach was utilized successfully to construct the tetracyclic skeleton of the angucyclinones. Late-stage acetonide deprotection challenges were overcome by A ring functional group manipulation, yielding a dihydroxy intermediate prior to the benzylic photo-oxidation, facilitating the total syntheses of angucyclinones 1-3. The key stereocenter was established through a known Sharpless asymmetric epoxidation/regioselective epoxide opening reaction.