Synthesis of Demissidine and Solanidine.

Zhang, Zhi-Dan; Shi, Yong; Wu, Jing-Jing; Lin, Jing-Rong; Tian, Wei-Sheng

Zhang, Zhi-Dan; Shi, Yong; Wu, Jing-Jing; Lin, Jing-Rong; Tian, Wei-Sheng.

Afiliación

Zhang ZD; Department of Chemistry, College of Life Sciences and Environment, Shanghai Normal University , 100 Guilin Road, Shanghai 200234, China.
Shi Y; Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
Wu JJ; Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
Lin JR; Department of Chemistry, College of Life Sciences and Environment, Shanghai Normal University , 100 Guilin Road, Shanghai 200234, China.
Tian WS; Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.

Org Lett ; 18(12): 3038-40, 2016 06 17.

Article en En | MEDLINE | ID: mdl-27232858

ABSTRACT

ABSTRACT

Demissidine and solanidine, two steroidal alkaloids, are synthesized in eight steps from tigogenin acetate and diosgenin acetate, respectively, which involve the replacement of three C-O bonds with C-N bonds. Key transformations include a cascade ring-switching process of furostan-26-acid, an epimerization of C25, an intramolecular Schmidt reaction, and an imine reduction/intramolecular aminolysis process.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2016 Tipo del documento: Article País de afiliación: China

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