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New Strategy for the Construction of a Monotetrahydrofuran Ring in Annonaceous Acetogenin Based on a Ruthenium Ring-Closing Metathesis: Application to the Synthesis of Solamin

โœ Scribed by Prestat, Guillaume; Baylon, Christophe; Heck, Marie-Pierre; Grasa, Gabriela A.; Nolan, Steven P.; Mioskowski, Charles


Book ID
126210628
Publisher
American Chemical Society
Year
2004
Tongue
English
Weight
83 KB
Volume
69
Category
Article
ISSN
0022-3263

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Application of the grubbs ring-closing m
โœ Seong Heon Kim; Israel Figueroa (in part); P.L. Fuchs ๐Ÿ“‚ Article ๐Ÿ“… 1997 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 235 KB

Metalation/alkylation of the pyrrole4used 10~ anion 15 regiospecifically yields the ~-alkylated ketones 16,17. Conversion of 17 to diene 24 followed by Grubbs ring-closing metathesis provides 29 which is transformed to the roseophilin tricyclic core structure 5.