363599-38-6Relevant articles and documents
Concise Asymmetric Syntheses of Streptazone A and Abikoviromycin**
W?rmer, Gustav J.,Villadsen, Nikolaj L.,N?rby, Peter,Poulsen, Thomas B.
, p. 10521 - 10525 (2021/03/29)
Streptazone A and abikoviromycin are alkaloids that both feature an unusual arrangement of reactive functionalities within a compact tricyclic ring system. Here, we report a highly concise asymmetric synthesis of both natural products. The route first constructs another family member, streptazone B1, using a rhodium-catalyzed distal selective allene-ynamide Pauson–Khand reaction. A regio- and enantioselective epoxidation under chiral phase-transfer catalytic conditions directly afforded streptazone A in 8 steps overall. In one additional step, a chemoselective, iridium-catalyzed reduction of the enaminone system then gave abikoviromycin. The reactivity of streptazone A towards a cysteine mimic, N-acetylcysteamine, was studied and revealed unanticipated transformations, including bis-thiol conjugation which may proceed via formation of a cyclopentadienone intermediate. With flexible access to these compounds, studies aimed to identify their direct biological targets are now possible.
Improved catalytic procedures for the copper(I)-promoted reactions of β-amido zinc reagents
Hunter,Jackson,Rami
, p. 1349 - 1352 (2007/10/03)
Copper-catalysed cross coupling of the β-aminoalkylzinc reagents 1a and 2 with unsaturated alkyl halides gives β-unsaturated ethylamines in 47-78% yield (4 examples) and enantiomerically pure β-unsaturated propylamines in 55-69% yield (3 examples). This m
