Palladium catalyzed synthesis of the furanoterpene ircinin-4

Citation
A. Furstner et al., Palladium catalyzed synthesis of the furanoterpene ircinin-4, SYNLETT, (1), 1999, pp. 29-32
Citations number
37
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
1
Year of publication
1999
Pages
29 - 32
Database
ISI
SICI code
0936-5214(199901):1<29:PCSOTF>2.0.ZU;2-9
Abstract
A flexible entry into 2,4-disubstituted furan derivatives is outlined emplo ying sulfonium salt 1 as a well accessible starting material. Condensation of the sulfur ylide derived from 1 with aldehydes, palladium catalyzed open ing of the vinyloxirane thus formed, and a final oxidative cyclization of t he furan ring constitute the key steps of this method. Its utility is exemp lified by the first total synthesis of the marine natural product ircinin-4 (2).