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