Synthesis of Solanum Alkaloid Demissidine Stereoisomers and Analogues

Demissidine is an indolizidine alkaloid isolated from several potato species. A simple synthesis of demissidine stereoisomers and analogues from a common steroidal sapogenin tigogenin is presented in the paper. The key intermediate in the synthesis of these compounds is readily available tigogenoic acid. Its step-by-step transformation to indolizidine yielded 20R,25R or 20R,25S products while the direct reductive amination produced the 20S,25R compound (25-epi-demissidine).

Automated summary

The paper presents a simple synthesis method of Demissidine stereoisomers and analogues from a common steroidal sapogenin tigogenin. Different stereoisomers and compounds were obtained through step-by-step transformation or direct reductive amination in the synthesis process.