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Synfacts 2021; 17(05): 0477
DOI: 10.1055/s-0040-1719774
Synthesis of Natural Products and Potential Drugs

Synthesis of (–)-Merrilactone A, (+)-Merrilactone B, and (–)-Anislactones A and B

Contributor(s):
Erick M. Carreira
,
Fabian Glatz
Shen Y, Li L, Xiao X, Yang S, Hua Y, Wang Y, Zhang Y.-w, *, Zhang Y. * Xiamen University, P. R. of China
Site-Specific Photochemical Desaturation Enables Divergent Syntheses of Illicium Sesquiterpenes.

J. Am. Chem. Soc. 2021;
143: 3256-3263
DOI: 10.1021/jacs.1c00525.
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Key words

(–)-merrilactone A - (+)-merrilactone B - (–)-anislactone A - (–)-anislactone B - photochemical desaturation - palladium catalysis - cyclization - radical cyclization

Significance

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.


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Comment

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.


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Publication History

Article published online:
20 April 2021

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