A novel synthesis of the cis-fused 2-oxA-3-decalone system present in vernolepin

✍ Scribed by F. Zutterman; P. De Clercq; M. Vandewalle

• Publisher: Elsevier Science
• Year: 1977
• Tongue: French
• Weight: 184 KB
• Volume: 18
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)83194-4

✦ Synopsis

Since the isolation and structural elucidation1 of vernolepin 1 and vernomenin 2, a substantial amount of research 2-5 has been performed, aimed at the synthesis of these novel elemanolide dilactones.

This recently culminated in their total synthesis2d'3e and in the synthesis of 8-desoxyvernolepin 2e 3. Both-vernolepin 1 and 8-desoxyvernolepin 3 show antitumor activity.

Several groups have focused their efforts on the synthesis of a functionalised cis-fused 2-oxa-3-decalone system, most approaches use rather long sequences involving as a rule cleavage of carbon-carbon bonds in a carbocyclic precursor. We therefore studied a novel approach which could lead directly to the key-compound 2 from which 2-oxa-3-decalones would easily be generated.