Concise Asymmetric Syntheses of Streptazone A and Abikoviromycin**

Streptazone A and abikoviromycin are alkaloids that both feature an unusual arrangement of reactive functionalities within a compact tricyclic ring system. Here, we report highly concise asymmetric synthesis natural products. The route first constructs another family member, streptazone B1, using rhodium-catalyzed distal selective allene-ynamide Pauson–Khand reaction. regio- enantioselective epoxidation under chiral phase-transfer catalytic conditions directly afforded in 8 steps overall. In one additional step, chemoselective, iridium-catalyzed reduction the enaminone system then gave abikoviromycin. reactivity towards cysteine mimic, N-acetylcysteamine, was studied revealed unanticipated transformations, including bis-thiol conjugation which may proceed via formation cyclopentadienone intermediate. With flexible access to these compounds, studies aimed identify their direct biological targets now possible.