Furans in synthesis 4. Silyl furans as butenolide equivalents

✍ Scribed by Steven P. Tanis; David B. Head

• Book ID: 104233830
• Publisher: Elsevier Science
• Year: 1984
• Tongue: French
• Weight: 247 KB
• Volume: 25
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)81464-7

✦ Synopsis

The preparation and utilization of butenolide anion equivalents alkylation sequences is described. Treatment with CH CO H unmas 1 and 6 in s a latent butenolide moiety providing a general route to 3-and34-alkyl 2(5H)-furanones. The butenolide moiety is present in numerous biologically active natural products, such as in the highly active neo-clerodanes ajugarins IV and V. 394 As part of a general program in furan chemistry, we were interested in developing substituted isoprenoid fury1 synthons 1 and 2 as the operational equivalents of butenolide anions $, and ,$ in the alkylation seauences outlined in equations 1 and 2.