Guaianolides : The total synthesis of (±)-estafiatin

✍ Scribed by M. Demuynck; A.A. Devreese; P.J. De Clercq; M. Vandewalle

• Book ID: 104220879
• Publisher: Elsevier Science
• Year: 1982
• Tongue: French
• Weight: 249 KB
• Volume: 23
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)87380-3

✦ Synopsis

An efficient synthesis of the trans fused perhydroazulenic epoxy ketone 2 is described. The potentiality of 2 is illustrated by its transformation into cf)-estafiatin 1.

Despite a long history, a wide distribution in nature, and extensive studies in relation to interconversions with other sesquiterpene classes2, no total synthesis of a naturally occurring guaianolide has been reported until re-cently3. This stands in sharp contrast with a large number of recent, successful approaches to the biogenetically related pseudoguaianolides4. From our experience this discrepancy in synthetic activities on both series is related to the different position of the 15-methyl substituent. In pseudoguaianolides the C-5 angular position of the methyl group is an important factor allowing good stereoand regiocontrol for the formation of other substituents.