Ring-closing metathesis: development of a cyclisation-cleavage strategy for the solid-phase synthesis of cyclic sulfonamides
Ring-closing metathesis: development of a cyclisation-cleavage strategy for the solid-phase synthesis of cyclic sulfonamides
A series of novel 7-membered cyclic sulfonamides have been synthesised using a solid-phase cyclisation - cleavage RCM strategy. Model solution studies indicated the sulfonamides were suitable substrates for RCM using the Grubbs' catalyst 2. Starting from either 2-carboxyethyl polystyrene (21) or Merrifield resin, various seven-membered sulfonamides were prepared in good to excellent yields at low catalyst loadings (2.5 - 5 mol%) using a flexible spacer between the polymer and the substrate. In addition, a novel double-armed linker was shown to allow efficient RCM cleavage of sulfonamides with as little as 1 mol% of the ruthenium alkylidene complex 2.
organic-synthesis, olefin metathesis, drug discovery, combinatorial
chemistry, traceless linkers, convenient method, building-blocks, peptidomimetics, libraries, ruthenium
835-844
Moriggi, J.D.
1ab863c1-f0fa-492c-a6c1-4c9f47f21b6e
Brown, Lynda J.
75aa95fa-5d27-46a7-9dbe-0f465a664f5b
Castro, José L.
a2111798-ae4d-47cd-969b-a52d69eb072a
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
2004
Moriggi, J.D.
1ab863c1-f0fa-492c-a6c1-4c9f47f21b6e
Brown, Lynda J.
75aa95fa-5d27-46a7-9dbe-0f465a664f5b
Castro, José L.
a2111798-ae4d-47cd-969b-a52d69eb072a
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Moriggi, J.D., Brown, Lynda J., Castro, José L. and Brown, Richard C.D.
(2004)
Ring-closing metathesis: development of a cyclisation-cleavage strategy for the solid-phase synthesis of cyclic sulfonamides.
Organic & Biomolecular Chemistry, 2 (6), .
(doi:10.1039/b313686h).
(PMID:15007411)
Abstract
A series of novel 7-membered cyclic sulfonamides have been synthesised using a solid-phase cyclisation - cleavage RCM strategy. Model solution studies indicated the sulfonamides were suitable substrates for RCM using the Grubbs' catalyst 2. Starting from either 2-carboxyethyl polystyrene (21) or Merrifield resin, various seven-membered sulfonamides were prepared in good to excellent yields at low catalyst loadings (2.5 - 5 mol%) using a flexible spacer between the polymer and the substrate. In addition, a novel double-armed linker was shown to allow efficient RCM cleavage of sulfonamides with as little as 1 mol% of the ruthenium alkylidene complex 2.
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Published date: 2004
Keywords:
organic-synthesis, olefin metathesis, drug discovery, combinatorial
chemistry, traceless linkers, convenient method, building-blocks, peptidomimetics, libraries, ruthenium
Identifiers
Local EPrints ID: 20291
URI: http://eprints.soton.ac.uk/id/eprint/20291
ISSN: 1477-0520
PURE UUID: 8c51256f-0ca1-41e4-98e7-a3788da6b0c0
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Date deposited: 20 Feb 2006
Last modified: 16 Mar 2024 03:00
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Author:
J.D. Moriggi
Author:
José L. Castro
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