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Stereoselective Total Synthesis of (±)-Alstoscholarisine E.

Michael D WoodDaniel W KlosowskiStephen F Martin
Published in: Organic letters (2019)
The shortest synthesis to date of (±)-alstoscholarisine E was accomplished in seven linear steps from commercially available reagents and 15.2% overall yield. The approach features a tandem vinylogous Mannich reaction and hetero-Diels-Alder reaction to access the core. A novel tactic to induce diastereoselective reduction of the cyclic vinyl ether was discovered, and a mild procedure to form the bridged aminal ring by partial reduction of the lactam ring via iridium-catalyzed hydrosilylation was developed.
Keyphrases
  • ionic liquid
  • electron transfer
  • gram negative