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

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

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 t...

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Veröffentlicht in:Journal of organic chemistry 2018-09, Vol.83 (18), p.11318-11322
Hauptverfasser: Siitonen, Juha H, Yu, Lu, Danielsson, Jakob, Di Gregorio, Giovanni, Somfai, Peter
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01540