Total Synthesis of the Proposed Structure of Uncarialin A

Journal of Organic Chemistry 2021
N.V Ūdris, Kristaps Jaudzems, Gints Šmits

The stereoselective total synthesis of the proposed structure of a potent serotonin 5-HT1A receptor agonist uncarialin A (1) is described. By employing the readily available meroquinene tert-butyl ester as the chiral synthon, the target structure has been prepared in a six-step linear sequence with a 17% overall yield. In comparison to the sample isolated from natural sources, the synthetic product shows significant spectral differences, strongly suggesting that the structure of the natural product should be revised.

Keywords
indole alkaloids, mitragynine, (-)-corynantheidine, quinolizidines, chemistry
DOI
10.1021/acs.joc.1c00324
Hyperlink
https://pubs.acs.org/doi/10.1021/acs.joc.1c00324

Ūdris, N., Jaudzems, K., Šmits, G. Total Synthesis of the Proposed Structure of Uncarialin A. Journal of Organic Chemistry, 2021, Vol. 86, No. 9, pp.6927-6930. ISSN 0022-3263. e-ISSN 1520-6904. Available from: doi:10.1021/acs.joc.1c00324

Publication language
English (en)