“Biomimetic” Cascade Reactions in Organic Synthesis: Construction of 4-Oxatricyclo[4.3.1.0]decan-2-one Systems and Total Synthesis of 1-O-Methylforbesione via Tandem Claisen Rearrangement/Diels–Alder Reactions

✍ Scribed by K. C. Nicolaou; Jim Li

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 133 KB
• Volume: 40
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/1521-3773(20011119)40:22<4264::aid-anie4264>3.0.co;2-1

✦ Synopsis

A further demonstration of the value of "biomimetically" inspired synthetic strategies toward natural products is provided by the title reactions that were developed for the construction of 4-oxatricyclo[4.3.1.0]decan-2-one systems from prochiral aromatic precursors. This biomimetic cascade was applied to the synthesis of 1-O-methylforbesione (2) from the prenylated xanthone 1 in one pot.