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Divergent Total Syntheses of Illicium Sesquiterpenes through Late-Stage Skeletal Reorganization.
Fu, Pengfei; Liu, Tao; Shen, Yang; Lei, Xin; Xiao, Tianjie; Chen, Peng; Qiu, Dongsheng; Wang, Zhen; Zhang, Yandong.
Afiliação
  • Fu P; State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, iCHEM, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China.
  • Liu T; State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, iCHEM, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China.
  • Shen Y; State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, iCHEM, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China.
  • Lei X; State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, iCHEM, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China.
  • Xiao T; State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, iCHEM, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China.
  • Chen P; State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, iCHEM, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China.
  • Qiu D; State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, iCHEM, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China.
  • Wang Z; State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, iCHEM, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China.
  • Zhang Y; State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, iCHEM, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China.
J Am Chem Soc ; 145(33): 18642-18648, 2023 08 23.
Article em En | MEDLINE | ID: mdl-37562030
ABSTRACT
We disclose unified, protecting-group-free, bioinspired divergent total syntheses of eight allo-cedrane and seco-prezizaane Illicium sesquiterpenes and formal syntheses of five anislactone sesquiterpenes. The efficiency of our approach derives from rapid access to the 15-carbon tricyclic carboxylic acid through cationic epoxide-ene cyclization and HAT oxygenation, transformation of this intermediate into three distinct tricyclic precursors via Lewis acid-mediated skeletal reorganizations, subsequent programmed oxidation level enhancement, and a biomimetic oxidation-initiated skeletal rearrangement cascade. Consequently, we created a synthetic correlation map of the three most prevalent Illicium sesquiterpene families.
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Texto completo: 1 Base de dados: MEDLINE Assunto principal: Sesquiterpenos / Illicium Limite: Humans Idioma: En Ano de publicação: 2023 Tipo de documento: Article
Texto completo
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Texto completo: 1 Base de dados: MEDLINE Assunto principal: Sesquiterpenos / Illicium Limite: Humans Idioma: En Ano de publicação: 2023 Tipo de documento: Article