Diastereospecific synthesis of spiro[4.5]decan-2-ones as vetivane precursor via rhodium catalysed Claisen rearrangement / hydroacylation

✍ Scribed by Tim Sattelkau; Peter Eilbracht

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 257 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)00197-x

✦ Synopsis

The one-pot combination of Claisen rearrangement of allyl vinyl ethers followed by an intramolecular hydroacylation catalysed by RhCl(cod)(dppe) is used as a key step in the synthesis of mesodimethyl-l,4-dioxa-dispiro[4.2.4.2]tetradecan-10-one ( 12). The diastereospecific outcome of the reaction is discussed. This product is a potential precursor in the synthesis of solavetivone.