Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 46, Pages 10439-10443Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202002404
Keywords
continuous-flow; eburnamine-vincamine alkaloids; hydrogenation; lactamization cascade; total synthesis; trans-selectivity
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Funding
- Fundamental Research Funds for the Central Universities [YJ201805, YJ201864]
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The Eburnamine-Vincamine alkaloids have been studied intensively over the past six decades for their outstandingly potent vasorelaxation activity. Stereocontrolled assembly of the C20/C21 adjacent chiral centers has been a formidable challenge in the synthesis of this family. Herein, we report a concise stereoselective total synthesis of twotrans-ring-fused non-natural analogues, (-)-20-epi-Vincamine and (-)-20-epi-Eburnamonine, that features the following key steps: a) a continuous-flow oxidation/lactam alcoholysis cascade producing the symmetrical dihydro-beta-carboline diester precursors, and b) a highly stereoselective Ir/f-Binaphane-catalyzed hydrogenation/lactamization cascade leading to the privilegedtrans-(20R, 21S) lactam ester scaffold with high-level enantio- and diastereocontrol.
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