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Formal Synthesis of ent-Cephalotaxine Using a One-Pot Parham–Aldol Sequence

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journal contribution
posted on 2018-07-17, 00:00 authored by Juha H. Siitonen, Lu Yu, Jakob Danielsson, Giovanni Di Gregorio, Peter Somfai
A short formal synthesis of ent-Cephalotaxine is achieved. The approach features a new Lewis acid-mediated [2,3]-Stevens rearrangement of N-allylated prolineamide to generate a key quaternary stereogenic center. Additionally, a one-pot Parham–aldol sequence was developed to rapidly assemble two of the four rings in the cephalotaxine core.