Racemic latifine (+)-(1), a new representative of the rare phenolic Amaryllidaceae alkaloids, has been synthesized by employing the Claisen rearrangement of 4-benzyloxycinnamyl 2-methoxyphenyl ether (11) as a key step. Based on the racemic synthesis, (R)-(+)-latifine (R)-(1), the unnatural enantiomer, has also been synthesized from (S)-O-benzylglycidol (S)-(3)via(S)-1-benzyloxy-3-phenylthio-propan-2-ol (S)-(4) as a key intermediate.
S. Takano, M. Akiyama and K. Ogasawara, J. Chem. Soc., Perkin Trans. 1, 1985, 2447 DOI: 10.1039/P19850002447
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