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New synthetic methodology for ring expansion of n-sized conjugated cycloalkenones into homoallylic n+3 lactones: 3-step synthesis of fragrant phoracantholide

✍ Scribed by Gary H Posner; Qiang Wang; Bethany A Halford; Jeffrey S Elias; John P Maxwell

Book ID: 104211286
Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 74 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01739-1

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✦ Synopsis

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, sequential reactions.

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