Biomimetic Total Syntheses of (-)-Leucoridines A and C through the Dimerization of (-)-Dihydrovalparicine

Angewandte Chemie
Praveen KokkondaRodrigo B Andrade

Abstract

Concise biomimetic syntheses of the Strychnos-Strychnos-type bis-indole alkaloids (-)-leucoridine A (1) and C (2) were accomplished through the biomimetic dimerization of (-)-dihydrovalparicine (3). En route to 3, the known alkaloids (+)-geissoschizoline (8) and (-)-dehydrogeissoschizoline (10) were also prepared. DFT calculations were employed to elucidate the mechanism, which favors a stepwise aza-Michael/spirocyclization sequence over the alternate hetero-Diels-Alder cycloaddition reaction.

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Citations

Mar 31, 2017·Organic Letters·Dan WangShuanhu Gao
Nov 24, 2017·Natural Product Reports·Wen-Ju Bai, Xiqing Wang
Oct 3, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ramiro F Quijano-QuiñonesDavid Cáceres-Castillo
Sep 3, 2019·The Journal of Organic Chemistry·Jian ZhangXiao-Qi Zhang
Aug 14, 2020·Journal of Natural Products·Manish WaliaRodrigo B Andrade

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