Protecting Group-Free Total Synthesis of (−)-Lannotinidine B
Journal of the American Chemical SocietyPublished 16 July 2012
Hui Ming Ge, Lande Zhang, Ren Xiang Tan, Zhu‐Jun Yao
Citations67
SJR quartileQ1
SJR score5.55
SNIP2.61
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TL;DR
The first total synthesis of (-)-lannotinidine B, a unique tetracyclic constitutent of Lycopodium annotinum, has been accomplished in 10 steps with 23% overall yield.
Abstract
The first total synthesis of (-)-lannotinidine B, a unique tetracyclic constitutent of Lycopodium annotinum, 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 trans-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.
Keywords
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