Total synthesis of (–)-luminacin D
Total synthesis of (–)-luminacin D
A second generation synthesis of (?)-luminacin D based on an early stage introduction of the trisubstituted epoxide group is reported, allowing access to the natural product in an improved yield and a reduced number of steps (5.4%, 17 steps vs 2.6%, 19 steps). A full account of the optimization work is provided, with the reversal of stereoselection in the formation of the C4 alcohol in equally excellent diastereoselectivity as key improvement.
3818-3837
Malassis, Julien
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Bartlett, Nathan
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Hands, Kane
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Selby, Matthew D.
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Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Malassis, Julien
5cd4224d-e4db-4835-863c-56b709511ccd
Bartlett, Nathan
ffb0225f-b68c-44d8-8a21-cfc86c17f606
Hands, Kane
97004965-f2fa-4d28-939f-cdf07666c49f
Selby, Matthew D.
6683489b-1c6c-4be4-99b4-f26f62e5e750
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Malassis, Julien, Bartlett, Nathan, Hands, Kane, Selby, Matthew D. and Linclau, Bruno
(2016)
Total synthesis of (–)-luminacin D.
Journal of Organic Chemistry, 81 (9), .
(doi:10.1021/acs.joc.6b00489).
Abstract
A second generation synthesis of (?)-luminacin D based on an early stage introduction of the trisubstituted epoxide group is reported, allowing access to the natural product in an improved yield and a reduced number of steps (5.4%, 17 steps vs 2.6%, 19 steps). A full account of the optimization work is provided, with the reversal of stereoselection in the formation of the C4 alcohol in equally excellent diastereoselectivity as key improvement.
Text
Lum D JOC_v32-changes accepted.pdf
- Accepted Manuscript
Other
acs.joc.6b00489
- Version of Record
More information
Accepted/In Press date: 7 April 2016
e-pub ahead of print date: 19 April 2016
Organisations:
Organic Chemistry: Synthesis, Catalysis and Flow
Identifiers
Local EPrints ID: 392805
URI: http://eprints.soton.ac.uk/id/eprint/392805
ISSN: 0022-3263
PURE UUID: 8b856496-1171-4b97-bdba-70177a2e4e53
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Date deposited: 18 Apr 2016 11:15
Last modified: 15 Mar 2024 05:29
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Contributors
Author:
Julien Malassis
Author:
Nathan Bartlett
Author:
Kane Hands
Author:
Matthew D. Selby
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