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2. Stereocontrolled synthesis of (-)-galanthamine

Author

Richard C. D. Brown, Nicholas P. Camp, Vachiraporn Satcharoen, Stephen C. Kemp, and Neville J. McLean

Subjects
Enyne, Molecular Structure, Stereochemistry, Galantamine, Aryl, Organic Chemistry, Enantioselective synthesis, Alcohol, Ether, Stereoisomerism, General Medicine, Isovanillin, Metathesis, Ring (chemistry), Biochemistry, chemistry.chemical_compound, chemistry, Cyclization, Organic chemistry, Physical and Theoretical Chemistry
Abstract

An enantioselective synthesis of (-)-galanthamine has been realized in 11 linear steps starting from isovanillin. A Mitsunobu aryl ether forming reaction was used to assemble the galanthamine backbone, which was stitched together using enyne ring-closing metathesis, Heck, and N-alkylation reactions affording the tetracyclic ring system. Control of relative and absolute stereochemistry was derived from an easily accessible enantiomerically enriched propargylic alcohol 13.

Published
2007

3. Synthesis of (-)-Galanthamine

Author

Stephen C. Kemp, Nicholas P. Camp, Richard C. D. Brown, Neville McLean, and V. Satcharoen

Subjects
Ring-closing metathesis, Chemistry, Heck reaction, Combinatorial chemistry
Published
2007

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