Synthesis of lupiwighteone via a para-Claisen–Cope rearrangement
2003; Elsevier BV; Volume: 59; Issue: 23 Linguagem: Inglês
10.1016/s0040-4020(03)00579-9
ISSN1464-5416
AutoresNawaf Al‐Maharik, Nigel P. Botting,
Tópico(s)Natural product bioactivities and synthesis
ResumoThe lanthanide catalysed para-Claisen–Cope rearrangement has been used as the key step in a short synthesis of the prenylated isoflavone, lupiwighteone. The Mitsunobu reaction was employed for the 5-O-prenylation of the acid/base sensitive acetylated isoflavone to afford the allyl aryl ether precursor, which was then rearranged under mild conditions in good yield. Rearrangement of the isoflavone gave the 8-prenylisoflavone as a single product, in good yield.
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