4 years ago

Divergent Synthesis of Solanidine and 22-epi-Solanidine

Divergent Synthesis of Solanidine and 22-epi-Solanidine
Wei-Sheng Tian, Yong Shi, Ling-Li Hou, Qing-Xiong Yang, Jing-Jing Wu, Zhi-Dan Zhang
A divergent synthesis of solanidine and 22-epi-solanidine, two 25S natural steroidal alkaloids, from 25R-configured diosgenin acetate, is described. Initially, solanidine was synthesized through a series of transformations including a cascade ring-switching process of furostan-26-acid, an epimerization of C25 controlled by the conformation of six-membered lactone ring, an intramolecular Schmidt reaction, and an imine reduction/intramolecular aminolysis process. To address the epimerization issue during Schmidt reaction, an improved synthesis was developed, which also led to a synthesis of 22-epi-solanidine. In this synthesis, selective transformation of azido lactone to azido diol and amino diol was realized through a reduction relay tactic. The azido diol was transformed to solanidine via an intramolecular Schmidt reaction/N-alkylation/reduction process and to 22-epi-solanidine via an intramolecular double N-alkylation process.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01133

DOI: 10.1021/acs.joc.7b01133

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