Synthesis of Solanum Alkaloid Demissidine Stereoisomers and Analogues
- 4 January 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 86 (2), 1575-1582
- https://doi.org/10.1021/acs.joc.0c02410
Abstract
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).Keywords
Funding Information
- Narodowe Centrum Nauki (2015/17/B/ST5/02892)
- Consejo Nacional de Ciencia y Tecnolog?a (462529)
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