Synthesis of Demissidine and Solanidine

  • Org Lett. 2016 Jun 17;18(12):3038-40. doi: 10.1021/acs.orglett.6b01320.
Zhi-Dan Zhang  1 ,  Yong Shi  2 ,  Jing-Jing Wu  2 ,  Jing-Rong Lin  1 ,  Wei-Sheng Tian  2
Affiliations
  • 1. Department of Chemistry, College of Life Sciences and Environment, Shanghai Normal University , 100 Guilin Road, Shanghai 200234, China.
  • 2. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
PMID: 27232858 DOI: 10.1021/acs.orglett.6b01320
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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