Protecting group-free total synthesis of (-)-lannotinidine B.
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.
State Key Laboratory of Coordination Chemistry, Nanjing National Laboratory of Microstructures, Institute of Chemical Biology and Drug Innovation, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.
Hui Ming
HM
Ge
Lan-De
LD
Zhang
Ren Xiang
RX
Tan
Zhu-Jun
ZJ
Yao
D000586:Amination; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D032502:Lycopodium / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D003517:Cyclopentanes; D006576:Heterocyclic Compounds, 4 or More Rings; C576685:lannotinidine B; C007201:cyclopentanone