1. Asymmetric Total Synthesis of Sarpagine and Koumine Alkaloids.
- Author
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Yang Z, Tan Q, Jiang Y, Yang J, Su X, Qiao Z, Zhou W, He L, Qiu H, and Zhang M
- Subjects
- Indole Alkaloids chemistry, Molecular Conformation, Stereoisomerism, Indole Alkaloids chemical synthesis
- Abstract
We report here a concise, collective, and asymmetric total synthesis of sarpagine alkaloids and biogenetically related koumine alkaloids, which structurally feature a rigid cage scaffold, with L-tryptophan as the starting material. Two key bridged skeleton-forming reactions, namely tandem sequential oxidative cyclopropanol ring-opening cyclization and ketone α-allenylation, ensure concurrent assembly of the caged sarpagine scaffold and installation of requisite derivative handles. With a common caged intermediate as the branch point, by taking advantage of ketone and allene groups therein, total synthesis of five sarpagine alkaloids (affinisine, normacusine B, trinervine, N
a -methyl-16-epipericyclivine, and vellosimine) with various substituents and three koumine alkaloids (koumine, koumimine, and N-demethylkoumine) with more complex cage scaffolds has been accomplished., (© 2021 Wiley-VCH GmbH.)- Published
- 2021
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