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New Silicon-Mediated, Sequential Ring Expansions of n -Sized 2-Cycloalkenones into Hydroxyolefinic n + m + p Medium-Sized Lactones: Short Synthesis of (−)-Phoracantholide-J

✍ Scribed by Posner, Gary H.; Hatcher, Mark A.; Maio, William A.


Book ID
127324814
Publisher
American Chemical Society
Year
2005
Tongue
English
Weight
68 KB
Volume
7
Category
Article
ISSN
1523-7060

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New synthetic methodology for ring expan
✍ Gary H Posner; Qiang Wang; Bethany A Halford; Jeffrey S Elias; John P Maxwell 📂 Article 📅 2000 🏛 Elsevier Science 🌐 French ⚖ 74 KB

Under the influence of Lewis acidic boron trifluoride-diethyl etherate, epoxides are activated sufficiently to undergo rapid nucleophilic opening by ketone enolate ions at -78°C, forming useful g-lactols. Application of this protocol to n+3 ring expansion features one-flask, multicomponent, sequent