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ChemInform Abstract: New Radical Reaction of S-Alkoxycarbonyl Xanthates. Total Synthesis of (.+-.)-Cinnamolide and (.+-.)-Methylenolactocin.

✍ Scribed by Judith E. Forbes; Radomir N. Saicic; Samir Z. Zard

Publisher
John Wiley and Sons
Year
2010
Weight
41 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

New Radical Reaction of S-Alkoxycarbonyl Xanthates. Total Synthesis of (Β±)-Cinnamolide and (Β±)-Methylenolactocin. -The irradiation of a variety of title xanthates, derived from the corresponding alcohols, gives either decarboxylated products such as (II) and (IV) or lactones like (VI), (IX), and (XII) as products of intramolecular addition. They readily undergo Ξ²-elimination of the xanthate group to afford exo-methylene lactones. These new reactions are applied to the synthesis of title terpenoid (XIX) and antibiotic (XXVI). -(FORBES, JUDITH E.

πŸ“œ SIMILAR VOLUMES

ChemInform Abstract: A Practical Modific
ChemInform Abstract: A Practical Modification of the Barton-McCombie Reaction and Radical O- to S-Rearrangement of Xanthates.
✍ Beatrice Quiclet-Sire; Samir Z. Zard πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 29 KB πŸ‘ 2 views

## A Practical Modification of the Barton-McCombie Reaction and Radical O-to S-Rearrangement of Xanthates. -A novel method for the title reaction avoiding toxic or expensive reagents is presented. It is noteworthy that in benzene as solvent the O-to S-rearranged compound is the major product. -(