In:
Angewandte Chemie International Edition, Wiley, Vol. 60, No. 23 ( 2021-06), p. 13105-13111
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.
Type of Medium:
Online Resource
ISSN:
1433-7851
,
1521-3773
DOI:
10.1002/anie.202102416
Language:
English
Publisher:
Wiley
Publication Date:
2021
detail.hit.zdb_id:
2011836-3
detail.hit.zdb_id:
123227-7
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