Short, Enantioselective Total Syntheses of (−)‐8‐Demethoxyrunanine and (−)‐Cepharatines A, C, and D

Abstract

Alle gemeinsam! Eine vereinheitlichte Synthesestrategie ermöglichte die erste enantioselektive Totalsynthese der Naturstoffe 8‐Demethoxyrunanin, Cepharatin A, Cepharatin C und Cepharatin D.

Boehringer Ingelheim New Investigator Award in Organic Chemistry: A. G. Doyle / Boehringer Ingelheim New Faculty Grant: S. E. Reisman / GDCh Prize for Authors and Journalists: V. Köster

“…Reisman’s research group is interested in new chemical reactions in the context of the total synthesis of natural products. She has reported on the total syntheses of (−)‐8‐demethoxyrunanine and (−)‐cepharatines A, C, and D in Angewandte Chemie 2…”

Boehringer Ingelheim New Investigator Award in organischer Chemie: A. G. Doyle / Boehringer Ingelheim New Faculty Grant: S. E. Reisman / GDCh‐Preis für Schriftsteller und Journalisten: V. Köster

“…Reismans Forschungsgruppe befasst sich mit neuen chemischen Reaktionen im Hinblick auf die Totalsynthese von Naturstoffen. In der Angewandten Chemie erschien ein Bericht von ihr über die Totalsynthesen von (−)‐8‐Demethoxyrunanin sowie den (−)‐Cepharatinen A, C und D 2…”

Unified divergent strategy towards the total synthesis of the three sub-classes of hasubanan alkaloids

“…Concurrently, Reisman and co-workers designed a general strategy involving a diastereoselective addition of Grignard reagent 16 to chiral N - tert -butanesulfinimine 17 for the generation of C14 tetrasubstituted stereocenter in 18 (Fig. 1d ) 32 . A divergent synthesis of (-)-8-demethoxyrunanine and (-)-cepharatines A ( 5 ), C ( 6 ), and D ( 8 ), belonging to the hasubanan subgroups B and C , respectively, were successfully realized from the common intermediate 18 .…”