Transition-metal-mediated chemo- and stereoselective total synthesis of (−)-galanthamine
Transition-metal-mediated chemo- and stereoselective total synthesis of (−)-galanthamine
An asymmetric synthetic route to (−)-galanthamine (1), a pharmacologically active Amaryllidaceae alkaloid used for the symptomatic treatment of early onset Alzheimer’s disease, was successfully established with very high levels of stereocontrol. The key to achieving high chemo- and stereo-selectivity in this approach was the use of transition-metal-mediated reactions, namely, enyne ring-closing metathesis, Heck coupling, and titanium-based asymmetric allylation.
1325-1334
Miller, Iain
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McLean, Neville J.
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Moustafa, Gamal
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Ajavakom, Vachiraporn
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Kemp, Stephen C
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Bellingham, Richard K.
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Camp, Nicholas P.
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Brown, Richard C.D.
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10 January 2022
Miller, Iain
20dd868b-5c11-4b6d-9d30-a397c92c2ac2
McLean, Neville J.
442ed7d5-0f16-4c0f-8fed-c4437aa800cc
Moustafa, Gamal
1a452cdc-4856-4243-9864-b391fb115f07
Ajavakom, Vachiraporn
f993a9cd-e859-41c0-995b-a40f1bf19a7c
Kemp, Stephen C
90bfffca-b4a8-48a4-b732-f6e709d4819b
Bellingham, Richard K.
ffa421f3-f2fb-4de9-b3f1-bba3f18b8976
Camp, Nicholas P.
4f21b310-272b-4c01-8c6b-60d36046cb28
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Miller, Iain, McLean, Neville J., Moustafa, Gamal, Ajavakom, Vachiraporn, Kemp, Stephen C, Bellingham, Richard K., Camp, Nicholas P. and Brown, Richard C.D.
(2022)
Transition-metal-mediated chemo- and stereoselective total synthesis of (−)-galanthamine.
The Journal of Organic Chemistry, 87 (2), .
(doi:10.1021/acs.joc.1c02638).
Abstract
An asymmetric synthetic route to (−)-galanthamine (1), a pharmacologically active Amaryllidaceae alkaloid used for the symptomatic treatment of early onset Alzheimer’s disease, was successfully established with very high levels of stereocontrol. The key to achieving high chemo- and stereo-selectivity in this approach was the use of transition-metal-mediated reactions, namely, enyne ring-closing metathesis, Heck coupling, and titanium-based asymmetric allylation.
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Published date: 10 January 2022
Additional Information:
Funding Information:
The authors acknowledge The Royal Society (R.C.D.B., University Research Fellowship), Eli Lilly (S.C.K., studentship), The University of Southampton (V.A., studentship), and EPSRC (I.R.M., S.C.K., and N.J.M., studentships) for financial support.
Publisher Copyright:
© 2022 American Chemical Society
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Local EPrints ID: 454351
URI: http://eprints.soton.ac.uk/id/eprint/454351
ISSN: 0022-3263
PURE UUID: 367d1a1c-8e0d-4492-98f6-25a2066312ea
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Date deposited: 08 Feb 2022 17:30
Last modified: 17 Mar 2024 03:55
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Contributors
Author:
Iain Miller
Author:
Neville J. McLean
Author:
Vachiraporn Ajavakom
Author:
Stephen C Kemp
Author:
Richard K. Bellingham
Author:
Nicholas P. Camp
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