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Stereocontrol by quaternary centres: a stereoselective synthesis of (?)-luminacin D

Stereocontrol by quaternary centres: a stereoselective synthesis of (?)-luminacin D
Stereocontrol by quaternary centres: a stereoselective synthesis of (?)-luminacin D
Very high diastereoselectivity can be achieved by 1,3-chelation-controlled allylation of aldehydes that possess a non-chelating ?-ether substituent, even if the ?-position is a quaternary centre and/or a spiro-epoxide. This reaction was used as a key step in an enantioselective synthesis of the angiogenesis inhibitor luminacin?D
0947-6539
3306-3310
Bartlett, Nathan
d0747614-b7a6-4856-b9ad-4367e13339e7
Gross, Leona
3d300e24-a3e5-4d82-93ae-68d744a8e1ed
Péron, Florent
8302b45b-82f0-4be5-af47-4a652fc22f2f
Asby, Daniel J.
cf0462d7-e923-45eb-b4ce-7c1673f544d5
Selby, Matthew D.
6683489b-1c6c-4be4-99b4-f26f62e5e750
Tavassoli, Ali
d561cf8f-2669-46b5-b6e1-2016c85d63b2
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Bartlett, Nathan
d0747614-b7a6-4856-b9ad-4367e13339e7
Gross, Leona
3d300e24-a3e5-4d82-93ae-68d744a8e1ed
Péron, Florent
8302b45b-82f0-4be5-af47-4a652fc22f2f
Asby, Daniel J.
cf0462d7-e923-45eb-b4ce-7c1673f544d5
Selby, Matthew D.
6683489b-1c6c-4be4-99b4-f26f62e5e750
Tavassoli, Ali
d561cf8f-2669-46b5-b6e1-2016c85d63b2
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba

Bartlett, Nathan, Gross, Leona, Péron, Florent, Asby, Daniel J., Selby, Matthew D., Tavassoli, Ali and Linclau, Bruno (2014) Stereocontrol by quaternary centres: a stereoselective synthesis of (?)-luminacin D. Chemistry - A European Journal, 20 (12), 3306-3310. (doi:10.1002/chem.201304776). (PMID:24519660)

Record type: Article

Abstract

Very high diastereoselectivity can be achieved by 1,3-chelation-controlled allylation of aldehydes that possess a non-chelating ?-ether substituent, even if the ?-position is a quaternary centre and/or a spiro-epoxide. This reaction was used as a key step in an enantioselective synthesis of the angiogenesis inhibitor luminacin?D

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Linclau revised manuscript.pdf - Accepted Manuscript
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Published date: 2014

Identifiers

Local EPrints ID: 363589
URI: http://eprints.soton.ac.uk/id/eprint/363589
DOI: doi:10.1002/chem.201304776
ISSN: 0947-6539
PURE UUID: 83cb49f6-f627-4c38-a599-b09f24f99c4e
ORCID for Ali Tavassoli: ORCID iD orcid.org/0000-0002-7420-5063
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

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Date deposited: 27 Mar 2014 14:37
Last modified: 15 Mar 2024 03:26

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Contributors

Author: Nathan Bartlett
Author: Leona Gross
Author: Florent Péron
Author: Daniel J. Asby
Author: Matthew D. Selby
Author: Ali Tavassoli ORCID iD
Author: Bruno Linclau ORCID iD

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