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Total Synthesis of Periplanone‐B Via Intramolecular Diels‐Alder Reaction with Furan‐Diene and Allene‐Dienophile

1994; Wiley; Volume: 103; Issue: 7-8 Linguagem: Inglês

10.1002/bscb.19941030717

0037-9646

Tom De Geyter, Serge Cauwberghs, Pierre J. De Clercq,

Synthetic Organic Chemistry Methods

Abstract A synthetic route towards (±)‐periplanone‐B is described based on (i) an intramolecular Diels‐Alder reaction involving a furan‐diene and an allene‐dienophile, (ii) selective (C‐O)‐cleavage in the resulting adduct by lithium di‐ tert ‐butylbiphenyl radical anion; (iii) a Grob fragmentation leading to the ten‐membered ring, as key‐steps.