38704-36-8Relevant articles and documents
Concise Asymmetric Syntheses of Streptazone A and Abikoviromycin**
W?rmer, Gustav J.,Villadsen, Nikolaj L.,N?rby, Peter,Poulsen, Thomas B.
supporting information, 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.
Some properties of SF-973 B substance, the enzyme catalyzing the conversion of dihydroabikoviromycin to abikoviromycin.
Tsuruoka,Shomura,Ogawa,Ezaki,Watanabe
, p. 168 - 174 (2007/10/08)
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Application of carbon 13 in biosynthetic studies; FT 13C nuclear magnetic resonance spectra of dihydrolatumcidin
Seto,Sato,Yonehara,Jankowski
, p. 609 - 611 (2007/10/10)
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