Gram-Scale Enantioselective Synthesis of (+)-Lucidumone

Autor:	Guanghao Huang, Cyrille Kouklovsky, Aurélien de la Torre
Rok vydání:	2022
Předmět:	Biological Products Lactones Colloid and Surface Chemistry Cycloaddition Reaction Electrons Stereoisomerism General Chemistry Biochemistry Catalysis
Zdroj:	Journal of the American Chemical Society. 144:17803-17807
ISSN:	1520-5126 0002-7863
DOI:	10.1021/jacs.2c08760
Popis:	The first enantioselective total synthesis of (+)-lucidumone is described through a 13-step synthetic pathway (longest linear sequence). The key steps involve the formation of a bridged bicyclic lactone by an enantioselective inverse-electron-demand Diels-Alder cycloaddition, C-O bond formation to assemble two fragments, and a one-pot retro-[4 + 2]/[4 + 2] cycloaddition cascade. The synthesis is scalable, and more than one gram of natural product was synthesized in one batch.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::fbb7f5b4d2610b3ded952283172075b9 https://doi.org/10.1021/jacs.2c08760 Zobrazit plný text záznamu