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Total Synthesis of (+)‐Gelsedine
Author(s) -
Beyersbergen van Henegouwen Winfred G.,
Fieseler Rutger M.,
Rutjes Floris P. J. T.,
Hiemstra Henk
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19990802)38:15<2214::aid-anie2214>3.0.co;2-v
Subject(s) - total synthesis , chemistry , oxindole , stereoselectivity , demethylation , allene , pyrrolizidine , stereochemistry , indole test , enantiomer , indole alkaloid , nitrogen atom , iodide , alkaloid , tartaric acid , malic acid , organic chemistry , catalysis , biochemistry , gene expression , dna methylation , citric acid , group (periodic table) , gene
A novel iodide‐promoted, allene‐terminated cyclization of an N ‐acyliminium ion, a stereoselective Heck spirocyclization, and a chemoselective demethylation at the nitrogen atom of an oxindole are the key transformations in the first total synthesis of the indole alkaloid (+)‐gelsedine ( 1 ). This dextrorotatory form of natural gelsedine was formed as a single enantiomer in 21 steps from ( S )‐malic acid.