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Synthesis of (–)-Merrilactone A, (+)-Merrilactone B, and (–)-Anislactones A and B
Site-Specific Photochemical Desaturation Enables Divergent Syntheses of Illicium Sesquiterpenes.
J. Am. Chem. Soc. 2021;
Key words(–)-merrilactone A - (+)-merrilactone B - (–)-anislactone A - (–)-anislactone B - photochemical desaturation - palladium catalysis - cyclization - radical cyclization
Zhang, Zhang and co-workers report the total synthesis of (–)-merrilactone A. Isolated from Illicium merrillianum, the natural product possesses potent neurotrophic activities. The highly oxygenated 5-5-4-5-5 ring system features an oxetane as well as two lactones. Further elaboration of intermediate H allows for the preparation of four additional Illicium sesquiterpenes.
Oxidative cyclization of ester B furnished lactone C, which was elaborated to alcohol D. Pd-catalyzed cyclization led to olefin E, which was transformed to selenocarbonate F. Radical cyclization gave rise to lactone G which was photochemically desaturated. Epoxidation of the resulting olefin H followed by acid-mediated ring opening furnished the natural product.
20 April 2021 (online)
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