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

The Journal of Organic Chemistry
Juha H SiitonenPeter Somfai

Abstract

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.

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Citations

Jun 8, 2021·Chemical Science·Benjamin D A ShennanDarren J Dixon
Jun 14, 2019·The Journal of Organic Chemistry·Hongjun JeonSanghee Kim
Feb 1, 2019·Organic Letters·Hongjun JeonSanghee Kim

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