Concise Total Synthesis of Salimabromide

Autor:	Hai-Hua Lu, Kang-Ji Gan, Fu-Qiang Ni, Zhihan Zhang, Yao Zhu
Rok vydání:	2022
Předmět:	Colloid and Surface Chemistry Cyclization Stereoisomerism General Chemistry Heterocyclic Compounds 4 or More Rings Biochemistry Carbon Catalysis
Zdroj:	Journal of the American Chemical Society. 144:18778-18783
ISSN:	1520-5126 0002-7863
DOI:	10.1021/jacs.2c08337
Popis:	We achieved a concise total synthesis of salimabromide by using a novel intramolecular radical cyclization to simultaneously construct the unique benzo-fused [4.3.1] carbon skeleton and the vicinal quaternary stereocenters. Other notable transformations include a tandem Michael/Mukaiyama aldol reaction to introduce most of the molecule's structural elements, along with hidden information for late-stage transformations, an intriguing tandem oxidative cyclization of a diene to form the bridged butyrolactone and enone moieties spontaneously, and a highly enantioselective hydrogenation of a cycloheptenone derivative (97% ee) that paved the way for the asymmetric synthesis of salimabromide.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::86a47eff7ff619773ad384753136bee0 https://doi.org/10.1021/jacs.2c08337 Zobrazit plný text záznamu