First asymmetric total syntheses of cernuane-type Lycopodium alkaloids, cernuine, and cermizine D.
The first total syntheses of two cernuane-type Lycopodium alkaloids, (-)-cernuine and (+)-cermizine D, were accomplished starting from (+)-citronellal. The syntheses involved organocatalytic alpha-amination to afford oxazolidinone, which is used for diastereoselective allylation, and asymmetric transfer aminoallylation followed by stereoselective construction of an aminal moiety as key steps.
Nishikawa
Yasuhiro
Y
Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
Kitajima
Mariko
M
Takayama
Hiromitsu
H
D000080462:Acyclic Monoterpenes; D000447:Aldehydes / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D000586:Amination; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D032502:Lycopodium / Q000737:chemistry*; D008968:Molecular Conformation; D039821:Monoterpenes / Q000737:chemistry; D023303:Oxazolidinones / Q000138:chemical synthesis / Q000737:chemistry; D054837:Quinolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000080462:Acyclic Monoterpenes; D000447:Aldehydes; D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; D039821:Monoterpenes; D023303:Oxazolidinones; D054837:Quinolizidines; C529947:cermizine D; C529946:cernuine; C108217:citronellal