Concise Total Synthesis of Salimabromide.
J Am Chem Soc
; 144(41): 18778-18783, 2022 10 19.
Article
em En
| MEDLINE
| ID: mdl-36194507
ABSTRACT
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.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Carbono
/
Compostos Heterocíclicos de 4 ou mais Anéis
Idioma:
En
Revista:
J Am Chem Soc
Ano de publicação:
2022
Tipo de documento:
Article
País de afiliação:
China