Angewandte Chemie - International Edition p. 13105 - 13111 (2021)
Update date:2022-08-05
Topics:
He, Ling
Jiang, Yan
Qiao, Zhen
Qiu, Hanyue
Su, Xiaojiao
Tan, Qiuyuan
Yang, Jiaojiao
Yang, Zhao
Zhang, Min
Zhou, Wenqiang
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, Na-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.
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