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- Title
Acyl Radical Addition to Activated Olefins: A Stereocontrolled Route to Polysubstituted Tetrahydrofurans and Lactones, and Application to the Total Synthesis of (+)-No. 2106 A.
- Authors
Grélaud, Simon; Lusseau, Jonathan; Landais, Yannick
- Abstract
The addition of acyl radicals to α,β-unsaturated esters, followed by acetalization and reduction of the resulting hemiacetal was shown to provide a straightforward access to tetrahydrofurans, and fused tetrahydrofuran-lactones in good yield with high 1,3-stereocontrol. Similar addition reactions to five- and six-membered-ring α-methylenelactones led to trisubstituted lactones with high diastereocontrol, using (Me3Si)3SiH as hydrogen-atom-transfer agent. This strategy was applied to the first total synthesis of (+)-No. 2106 A, a fused THF-lactone produced by an endophytic fungus isolated from the seeds of the mangrove Avicennia marina.
- Subjects
ACYL radicals; ADDITION reactions; ALKENES; LACTONES; HYDROGEN atom; ATOM transfer reactions
- Publication
European Journal of Organic Chemistry, 2017, Vol 2017, Issue 10, p1323
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201601624