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Concise total syntheses of two flavans and structure revision assisted by quantum NMR calculations.
Zhou, Tingting; Zheng, Anquan; Zhang, Wenge; Lu, Xiuxiang; Chen, Huiyu; Tan, Haibo.
Afiliação
  • Zhou T; Key Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, People's Republic of China. tanhaibo@scbg.ac.cn.
  • Zheng A; School of Pharmacy and Bioengineering, Chongqing University of Technology, Chongqing 400054, People's Republic of China.
  • Zhang W; Key Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, People's Republic of China. tanhaibo@scbg.ac.cn.
  • Lu X; School of Pharmacy and Bioengineering, Chongqing University of Technology, Chongqing 400054, People's Republic of China.
  • Chen H; Key Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, People's Republic of China. tanhaibo@scbg.ac.cn.
  • Tan H; Key Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, People's Republic of China. tanhaibo@scbg.ac.cn.
Org Biomol Chem ; 20(20): 4096-4100, 2022 05 26.
Article em En | MEDLINE | ID: mdl-35522925
ABSTRACT
A two-step protecting-group-free protocol for the synthesis of 3'-hydroxy-5,7-dimethoxy-4-O-2'-cycloflavan (1) and concise total synthesis of 4'-hydroxy-5,7-dimethoxy-4-O-2'-cycloflavan (8) enabled by a PTSA triggered bioinspired olefin isomerization/hemiacetalization/dehydration/[3 + 3]-type cycloaddition cascade reaction are reported. The successful synthesis of cycloflavan 8 along with GIAO 13C NMR calculations of flavan-4-ol 9 and cycloflavan 8 indicated the misassignment of the flavonoid isolated previously and realized the revision of its actual structure.
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Texto completo: 1 Coleções: 01-internacional Temas: Geral Base de dados: MEDLINE Assunto principal: Flavonoides / Polifenóis Idioma: En Revista: Org Biomol Chem Assunto da revista: BIOQUIMICA / QUIMICA Ano de publicação: 2022 Tipo de documento: Article
Texto completo
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Texto completo: 1 Coleções: 01-internacional Temas: Geral Base de dados: MEDLINE Assunto principal: Flavonoides / Polifenóis Idioma: En Revista: Org Biomol Chem Assunto da revista: BIOQUIMICA / QUIMICA Ano de publicação: 2022 Tipo de documento: Article