Total synthesis of (±)- and (+)-latifine
Abstract
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.