A facile protocol for the synthesis of highly substituted fused γ-alkylidene butenolides using direct annulation of ketones with α-ketoesters, via TiCl4-n-Bu3N mediated aldol addition followed by an intramolecular enol-lactonization/cyclization cascade, is reported.
A highly concise
bioinspired four-step total synthesis of yaoshanenolides
A and B possessing tricyclic spirolactone with an unusual 5′
H
-spiro-[bicyclo[2.2.2]-oct[2]ene-7,2′-furan]-5′-one
scaffold is reported. This synthesis features high-yielding aldol-type
addition of γ-butyrolactone on to the aldehyde, exocyclic olefination
of lactone derivative using Eschenmoser’s salt, and highly
facial- and endo-selective [4 + 2]-cycloaddition of fully functionalized
5-methylene-2(5
H
)-furanone with natural
R
-(−)-α-phellandrene. The approach allows access to yaoshanenolides
A and B in four linear steps in 11 and 13% overall yield.
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