Synthetic studies towards (+)-Dihydroampullicin. Michael addition of N-Boc-2-(tert-butyldimethylsiloxy)-3-methyl-pyrrole to α-methylene lactones

✍ Scribed by Isabel Marcos; Elena Redero; Francisco Bermejo

• Book ID: 104211049
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 106 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)01499-4

✦ Synopsis

The Michael addition of N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)-3-methyl-pyrrole (4) to several a-methylene lactones catalyzed by fluoride ions yielded the corresponding homologated products (26-30) with good yields. Application of this reaction to the sililoxy bicyclic lactone (5) allowed us to isolate the tricyclic lactone (26), a highly valuable intermediate in our synthetic strategy leading to the growth regulator (+)-Dihydroampullicin (1).