AI Article Synopsis
- - A new method for synthesizing resibufogenin and bufalin was developed using only seven steps without the need for protecting groups, starting from androstenedione (AD).
- - The synthesis involved introducing a hydroxyl group at C14 using hydroxylase P-450, which helped control the configuration at C17 during subsequent reactions.
- - The final steps included dehydrating the intermediate and using epoxidation to produce resibufogenin, while bufalin was synthesized through a more complex anaerobic Mukaiyama hydration process.
Article Abstract
A chemoenzymatic synthesis access to resibufogenin and bufalin was developed in seven steps without protecting groups. Starting with androstenedione (AD), an α-OH was introduced directly at C14 by hydroxylase P-450, which was further used as the directing group for hydrogenation to fully control the C17 configuration in the β-orientation after Suzuki cross-coupling. Dehydration of 14α-OH followed by an epoxidation delivered resibufogenin. Simultaneously, bufalin was also obtained via a challenging anaerobic Mukaiyama hydration.
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| http://dx.doi.org/10.1021/acs.orglett.4c03433 | DOI Listing |
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