The total synthesis of dl-yomogin

✍ Scribed by Drury Caine; Gerard Hasenhuettl

• Book ID: 104213514
• Publisher: Elsevier Science
• Year: 1975
• Tongue: French
• Weight: 182 KB
• Volume: 16
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)71972-1

✦ Synopsis

The sesquiterpene lactone yomogin k), isolated from Artemisia princeps Pamp. by Geismann,' contains a cross-conjugated dienone system of the a-santonin type as well as an a-methylene-ybutyrolactone grouping. Since dienones related to a-santonin readily undergo photochemical rearrangements into hydroazulene derivatives, 3 it appeared that yomogin (or some of its derivatives having the unsaturated lactone function protected) might serve as a useful material for the synthesis of certain cytotoxic guaianolides which also contain an a-methylene-y-butyrolactone grouping.4 Therefore, a total synthesis ofJ itself appeared to be of interest and has been carried out.