On the choice of Lewis acids for the Prins reaction; two total syntheses of (±)-Civet
On the choice of Lewis acids for the Prins reaction; two total syntheses of (±)-Civet
While developing new variations of the Prins cyclisation reaction, the effect of the choice of Lewis acid on the outcome of the reaction and the product(s) has been investigated, yielding hitherto unseen dihydropyran products in the Prins cyclisation reaction of homoallylic alcohols, and two new modifications of the reaction: the triflate-trapped Prins adduct and the Mukaiyama-Aldol-silyl-Prins reaction. Two of these methods are employed in two complementary total syntheses of the important perfumery compound, (+/-)-Civet.
5107-5124
Chio, Freda K.
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Warne, Julie
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Gough, Damien
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Penny, Mark
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Green, Sasa
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Coles, Simon J.
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Hursthouse, Mike B.
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Jones, Peter
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Hassall, Lorraine
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McGuire, Thomas M.
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Dobbs, Adrian P.
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8 July 2011
Chio, Freda K.
48bb8119-0eca-4f4a-bb78-47205438edfd
Warne, Julie
fe2c169d-1ac8-4208-905c-96c87107a750
Gough, Damien
52836da8-62d6-4dfb-a6ee-1840aa2ba771
Penny, Mark
4278e450-621d-4876-a797-87e4217d7020
Green, Sasa
49d67fcb-1fba-41e2-a10f-ebea32ab24dc
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Mike B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Jones, Peter
58b92f6d-0f66-43fa-bfa2-fcfbefd86535
Hassall, Lorraine
90a82cdf-7fa3-44f0-a160-61358c14a368
McGuire, Thomas M.
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Dobbs, Adrian P.
0e5c81d2-c250-47e4-a782-00984af2de54
Chio, Freda K., Warne, Julie, Gough, Damien, Penny, Mark, Green, Sasa, Coles, Simon J., Hursthouse, Mike B., Jones, Peter, Hassall, Lorraine, McGuire, Thomas M. and Dobbs, Adrian P.
(2011)
On the choice of Lewis acids for the Prins reaction; two total syntheses of (±)-Civet.
Tetrahedron, 67 (27-28), .
(doi:10.1016/j.tet.2011.05.019).
Abstract
While developing new variations of the Prins cyclisation reaction, the effect of the choice of Lewis acid on the outcome of the reaction and the product(s) has been investigated, yielding hitherto unseen dihydropyran products in the Prins cyclisation reaction of homoallylic alcohols, and two new modifications of the reaction: the triflate-trapped Prins adduct and the Mukaiyama-Aldol-silyl-Prins reaction. Two of these methods are employed in two complementary total syntheses of the important perfumery compound, (+/-)-Civet.
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Published date: 8 July 2011
Organisations:
Molecular Diagnostics & Thereputics
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Local EPrints ID: 346140
URI: http://eprints.soton.ac.uk/id/eprint/346140
ISSN: 0040-4020
PURE UUID: c4e446a4-3425-4c4d-a615-b5b5fefcfd89
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Date deposited: 20 Dec 2012 13:58
Last modified: 15 Mar 2024 03:01
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Author:
Freda K. Chio
Author:
Julie Warne
Author:
Damien Gough
Author:
Mark Penny
Author:
Sasa Green
Author:
Peter Jones
Author:
Lorraine Hassall
Author:
Thomas M. McGuire
Author:
Adrian P. Dobbs
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