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).

Citation

Juan A Rivas-Loaiza, Aneta Baj, Yliana López, Stanisław Witkowski, Agnieszka Wojtkielewicz, Jacek W Morzycki. Synthesis of Solanum Alkaloid Demissidine Stereoisomers and Analogues. The Journal of organic chemistry. 2021 Jan 15;86(2):1575-1582

PMID: 33393776

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