Stereocontrolled Synthesis of (−)-Galanthamine

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...

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Published in:Organic letters 2007-05, Vol.9 (10), p.1867-1869
Main Authors: Satcharoen, Vachiraporn, McLean, Neville J, Kemp, Stephen C, Camp, Nicholas P, Brown, Richard C. D
Format: Article
Language:English
Subjects:
Cyclization
Galantamine - chemical synthesis
Galantamine - chemistry
Molecular Structure
Stereoisomerism
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cited_by cdi_FETCH-LOGICAL-a379t-d1390fdf73b7112bf02ba40ec1cc98363b1268012ca6e652fbb4c5cc0cc83e743
cites cdi_FETCH-LOGICAL-a379t-d1390fdf73b7112bf02ba40ec1cc98363b1268012ca6e652fbb4c5cc0cc83e743
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creator Satcharoen, Vachiraporn
McLean, Neville J
Kemp, Stephen C
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description 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.
doi_str_mv 10.1021/ol070255i
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subjects Cyclization
Galantamine - chemical synthesis
Galantamine - chemistry
Molecular Structure
Stereoisomerism
title Stereocontrolled Synthesis of (−)-Galanthamine
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