Exploring an Alternative Synthetic Pathway for the Total Synthesis of (±)-Nordasycarpidol and (±)-Nordasycarpidone

A total synthesis of the strychnos alkaloids, dasycarpidol and nordasycarpidone, has been accomplished from 2-(3-ethyl-1-oxo-2,3,4,9-tetrahydro-1 H -carbazol-2-yl)acetonitrile 1 , which is the C-2 ethyl side chain of carbazole as well as carbazole-fused lactone 3 that is conveniently of the key azoc...

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Bibliographic Details
Published in:Chemistry of natural compounds 2023-07, Vol.59 (4), p.715-720
Main Authors: Uludag, Nesimi, Nevarsa, Alev Orhan
Format: Article
Language:English
Subjects:
Acetonitrile
alkaloids
Carbazoles
Carbonyl groups
Carbonyls
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
indoles
Natural products
NMR
Nuclear magnetic resonance
Organic Chemistry
Plant Sciences
spectroscopy
Strychnos
Synthesis
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Summary:A total synthesis of the strychnos alkaloids, dasycarpidol and nordasycarpidone, has been accomplished from 2-(3-ethyl-1-oxo-2,3,4,9-tetrahydro-1 H -carbazol-2-yl)acetonitrile 1 , which is the C-2 ethyl side chain of carbazole as well as carbazole-fused lactone 3 that is conveniently of the key azocino[4,3-b]indole skeleton 6 . These syntheses of the target natural products are accomplished without a protecting group, which has a carbonyl group at the C-1 position of the carbazole. These alternative routes are accomplished by shortening the number of steps with high efficiency and also nordasycarpidol 8 synthesized for the first time in the literature. The structures of all the presently synthesized compounds were confirmed using spectroscopic methods (FT-IR, 1 H NMR, 13 C NMR).
ISSN:0009-3130
1573-8388
DOI:10.1007/s10600-023-04095-4