Stereocontrolled synthesis of (-)-galanthamine
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 affording the tetracyclic ring system. Control of relative and absolute stereochemistry was derived from an easily accessible enantiomerically enriched propargylic alcohol 13.
intramolecular heck reaction, galantamine, galanthamine, alkaloids, dl-lycoramine, efficient total-synthesis, (+/-)-galanthamine, (+/-)-lycoramine, alzheimers-disease, ring-system, racemic lycoramine
1867-1869
Satcharoen, V.
df06227d-27fc-4a9e-a89e-72cacd366959
McLean, N.J.
9fe80e17-b6e3-4efd-8a21-e0904ba8f3f7
Kemp, S.C.
90bfffca-b4a8-48a4-b732-f6e709d4819b
Camp, N.P.
6976e25d-ca23-4013-85dd-f7eb1ac5f612
Brown, R.C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
2007
Satcharoen, V.
df06227d-27fc-4a9e-a89e-72cacd366959
McLean, N.J.
9fe80e17-b6e3-4efd-8a21-e0904ba8f3f7
Kemp, S.C.
90bfffca-b4a8-48a4-b732-f6e709d4819b
Camp, N.P.
6976e25d-ca23-4013-85dd-f7eb1ac5f612
Brown, R.C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Satcharoen, V., McLean, N.J., Kemp, S.C., Camp, N.P. and Brown, R.C.D.
(2007)
Stereocontrolled synthesis of (-)-galanthamine.
Organic Letters, 9 (10), .
(doi:10.1021/ol070255i).
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.
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Published date: 2007
Keywords:
intramolecular heck reaction, galantamine, galanthamine, alkaloids, dl-lycoramine, efficient total-synthesis, (+/-)-galanthamine, (+/-)-lycoramine, alzheimers-disease, ring-system, racemic lycoramine
Identifiers
Local EPrints ID: 54380
URI: http://eprints.soton.ac.uk/id/eprint/54380
ISSN: 1523-7060
PURE UUID: 6fdb44ae-66d4-413d-89bf-3bc6297a1d3c
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Date deposited: 01 Aug 2008
Last modified: 16 Mar 2024 02:54
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Contributors
Author:
V. Satcharoen
Author:
N.J. McLean
Author:
S.C. Kemp
Author:
N.P. Camp
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