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Lythranidine
Lythranidine is an alkaloid that was first isolated from the plant ''Lythrum anceps''. The compound requires eight steps to synthesize ''in vitro'' which requires the formation of a 17 membered ring with a trans-2,6-disubstituted piperidine ring. Lythranidine was first synthesized by Fuji Kaoru, Kohei Ichikawa and Eiichi Fujita in 1971.〔Lythraceous alkaloids. Part 11. Total synthesis of (±)-lythranidine. Kaoru Fuji , Kohei Ichikawa and Eiichi Fujita J. Chem. Soc., Perkin Trans. 1, 1980, 1066-1069〕 They were the first paper published on the synthesis of lythranidine. In 1991, a paper was published about the synthesis of lythranidine by William Carruthers , Peter Coggins and John B. Weston who had synthesized the compound in 11 steps using nitrone cycloaddition.〔Nitrone cycloaddition: an approach to the cyclophane alkaloid (±)-lythranidine. William Carruthers , Peter Coggins and John B. Weston J. Chem. Soc., Perkin Trans. 1, 1991, 611-616〕
== Synthesis ==
Lythranidine is classified as an alkaloid and it contains a piperidine group that defines the synthesis of the structure via nitrone cycloaddition. The synthesis of this compound can take 11 steps instead or 8 depending on if the reaction undergone is a nitrone cycloaddition.
The synthesis described below was taken from the Fujita et. al, 1980, 1651-1653
2,6-Bis(chloromethyl)pyridine is treated with three equivalents of triphenylphosphine and refluxed with dimethylformamide and is afforded the bisphosphonium salt. The salt is subsequently treated with sodium hydride in dichloromethane to form a ylide .Wittig reaction of the dialdehyde given in the paper with another alkaloid in the lythracae family under high dilution conditions yielded the cyclophane. On dehydrogenation over palladium-charcoal, the reactant forms the 17 membered ring. The 17 membered ring with n-chloroperbenzoic acid was hydrogenolysed over palladium-charcoal ; subsequent acetylation with acetic anhydride-triethylamine yielded lythranidine in the stereoisomer shown. In the nitrone cycoladdition synthesis, when the pyridine is reduced, it forms a cis product and the product wanted is trans. The cis product was treated with formic acid and formalin to create the trans product.〔Lythraceous alkaloids. Part IV. Structure and absolute configuration of lythranine, lythranidine, and lythramine E. Fujita and K. Fuji J. Chem. Soc. C, 1971, 1651-1653〕
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