Protecting Group-Free Total Synthesis of (−)-Lannotinidine B

The first total synthesis of (−)-lannotinidine B, a unique tetracyclic constitutent of <i>Lycopodium annotinum</i>, has been accomplished in 10 steps with 23% overall yield. The completed short and efficient synthesis is characterized with three highly chemo- and/or stereoselective reductive-amination steps to furnish the desired <i>trans</i>-fused 6/6 bicycle and the aza seven-membered ring system, and a direct intramolecular acyloin condensation to deliver the cyclopentanone moiety, as well as successful application of a protecting group-free strategy and an optimal redox order

Protecting Group-Free Total Synthesis of (−)-Lannotinidine B

The first total synthesis of (−)-lannotinidine B, a unique tetracyclic constitutent of <i>Lycopodium annotinum</i>, has been accomplished in 10 steps with 23% overall yield. The completed short and efficient synthesis is characterized with three highly chemo- and/or stereoselective reductive-amination steps to furnish the desired <i>trans</i>-fused 6/6 bicycle and the aza seven-membered ring system, and a direct intramolecular acyloin condensation to deliver the cyclopentanone moiety, as well as successful application of a protecting group-free strategy and an optimal redox order

Enantioselective Total Synthesis of Lycoposerramine‑Z Using Chiral Phosphoric Acid Catalyzed Intramolecular Michael Addition

A new enantioselective total synthesis of phlegmarine-type <i>Lycopodium</i> alkaloid lycoposerramine-Z (<b>1</b>) has been accomplished, using one-pot chemoselective sequential additions of two different Grignard reagents to the bis-Weinreb-amide intermediate and an efficient construction of the fully fuctionalized cyclohexanone intermediate with a chiral phosphoric acid catalyzed enantioselective intramolecular Michael addition