Total synthesis of (+/-)-halomon by a Johnson-Claisen rearrangement by Schlama, T, Baati, R, Gouverneur, V, Valleix, A, Falck, JR, Mioskowski, C

An enantioselective epoxide rearrangement - Claisen rearrangement approach to prostaglandins and (+)-iridomyrmecin by Hodgson, D, Gibbs, A

“…The asymmetric syntheses of prostaglandin precursor 8 and (+)iridomyrmecin (12) via highly enantioselective rearrangement of the epoxide 1 and subsequent Ireland-Claisen rearrangement are described.…”

The Claisen rearrangement approach to fused bicyclic medium-ring oxacycles. by Burton, J, Anderson, E, O'Sullivan, P, Collins, I, Davies, J, Bond, A, Feeder, N, Holmes, AB

“…The synthesis of five fused-bicyclic medium-ring lactones carrying identical ring-fusion to that in the polyether toxins is described using an enolate hydroxylation, intramolecular hydrosilation, Claisen rearrangement sequence.…”

Doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements. by Davies, S, Garner, A, Nicholson, R, Osborne, J, Roberts, P, Savory, E, Smith, A, Thomson, J

“…The doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangement of silylketene aminals derived from 5-substituted (3S,4E,alphaR)-1-benzyloxy-3-[N-acyl-N-(alpha-methylbenzyl)amino]pent-4-enes furnishes 2,3-disubstituted (R)-N-alpha-methylbenzyl (2S,3R,4E)-7-benzyloxyhept-4-enamides in >90% de under the "matched" control of both stereogenic centres. …”

Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements. by Davies, S, Garner, A, Nicholson, R, Osborne, J, Savory, E, Smith, A

“…Asymmetric [3,3]-sigmatropic aza-Claisen rearrangement of the (Z)-N-allyl-N,O-silylketene aminal of (3S,4E,alphaR)-1-benzyloxy-3-(N-propionyl-N-alpha-methylbenzylamino)hex-4-ene furnishes (2S,3R,4E,alphaR)-N-alpha-methylbenzyl-2,3-dimethyl-7-benzyloxyhept-4-enamide in > 92% d.e.; rearrangement of the diastereomeric (3R,4E,alphaR)-(Z)-N,O-silylketene aminal proceeds with low diastereoselectivity.…”

Synthesis of fused bicyclic medium-ring lactones via Claisen rearrangement by Burton, J, O'Sullivan, P, Anderson, E, Collins, I, Holmes, AB

“…Fused bicyclic medium-ring lactones, carrying identical ring-fusion to that in the polyether toxins, are prepared by a Claisen rearrangement sequence.…”

Synthesis of simplified analogues of eleutherobin via a Claisen rearrangement/RCM strategy by Mak, S, Chiang, G, Davidson, J, Davies, J, Ayscough, A, Pain, G, Burton, J, Holmes, AB

Synthesis of medium-ring lactones via tandem methylenation/Claisen rearrangement of cyclic carbonates by Davidson, J, Anderson, E, Buhr, W, Harrison, JR, O'Sullivan, P, Collins, I, Green, R, Holmes, AB

“…Tandem methylenation/Claisen rearrangement of cyclic carbonates derived from vinyl-substituted 1,3- and 1,4-diols afforded eight and nine-membered unsaturated lactones respectively.…”

Synthesis of medium-ring lactones via tandem methylenation/Claisen rearrangement of cyclic carbonates by Anderson, E, Davidson, J, Harrison, JR, O'Sullivan, P, Burton, J, Collins, I, Holmes, AB

“…The reaction proceeds by initial formation of a ketene acetal which undergoes subsequent in situ Claisen rearrangement to provide the corresponding lactones. …”

Asymmetric syntheses of enantiopure C(5)-substituted transpentacins via diastereoselective Ireland-Claisen rearrangements. by Davies, S, Fletcher, A, Roberts, P, Thomson, J, Zammit, C

“…Asymmetric syntheses of (S,S,S)-2-amino-5-methylcyclopentanecarboxylic acid and (S,S,S)-2-amino-5-phenylcyclopentanecarboxylic acid were achieved in 9 steps from commercially available starting materials via the Ireland-Claisen rearrangement of two enantiopure β-amino allyl esters, followed by ring-closing metathesis, reduction and deprotection. …”

Synthesis and Claisen rearrangement of bridged bicyclic enol ethers of relevance to the course of ketene s-cis-diene cycloaddition. by Robertson, J, Fowler, T

“…The synthesis is described of a range of 3-alkylidene-2-oxabicyclo[2.2.1]hept-5-ene and 3-alkylidene-2-oxabicyclo[2.2.2]oct-5-ene derivatives; Claisen rearrangement of these substrates either thermally or in the presence of an added Lewis acid results in the formation of bicyclic cyclobutanones with generally good conversions. …”

Diastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins. by Davies, S, Fletcher, A, Lee, J, Roberts, P, Souleymanou, M, Thomson, J, Zammit, C

“…The diastereoselective Ireland-Claisen rearrangement of a range of substituted allyl β-amino esters gave the corresponding enantiopure α-substituted-β-amino esters with good diastereoselectivity. …”

Access to a guanacastepene and cortistatin-related skeleton via ethynyl lactone Ireland−Claisen rearrangement and transannular (4 + 3)-cycloaddition of an azatrimethylenemethane diyl by Zhurakovskyi, O, Ellis, S, Thompson, A, Robertson, J

“…The cyclization precursors were prepared via the first reported examples of the Ireland–Claisen rearrangement of an ethynyl lactone.…”

An organocatalytic approach to the core of eunicellin. by Gilmour, R, Prior, T, Burton, J, Holmes, AB

“…A stereocontrolled synthesis of the core of eunicellin is described featuring a Claisen rearrangement and a diastereoselective organocatalytic Diels-Alder reaction as the key steps.…”

A short synthesis of aphanamol I in both racemic and enantiopure forms by Burton, J, Ferrara, S

“…Key steps include: a catalytic enantioselective conjugate addition, an oxidative radical cyclisation, and a ringexpanding Claisen rearrangement.…”

Synthesis of (+)-obtusenyne. by Mak, S, Curtis, N, Payne, A, Congreve, MS, Wildsmith, A, Francis, C, Davies, J, Pascu, S, Burton, J, Holmes, AB

“…An enantioselective synthesis of the halogenated medium-ring ether natural product (+)-obtusenyne is reported which uses the ring expansion of a seven-membered ketene acetal by means of a Claisen rearrangement to construct the core nine-membered oxygen heterocycle. …”

A Concise Synthesis of the Octalactins by O'Sullivan, P, Buhr, W, Fuhry, M, Harrison, JR, Davies, J, Feeder, N, Marshall, DR, Burton, J, Holmes, AB

“…Key steps include the Paterson-Aldol reaction for the rapid assembly of the carbonate 46, methylenation of 46 and subsequent Claisen rearrangement of the corresponding alkenyl-substituted cyclic ketene acetal to provide the core unsaturated medium-ring lactone 47, and the use of enzyme-mediated acetate deprotection in the presence of a medium-ring lactone.…”

Mechanism and applications of lithium amide-induced asymmetric rearrangements of 4-substituted and 4,4-disubstituted cyclopentene oxides to cyclopentenols by Hodgson, D, Gibbs, A, Drew, M

“…Also described are asymmetric syntheses of prostaglandin precursor 40 and (+)-iridomyrmecin (48) via highly enantioselective rearrangement of the epoxide 3 and subsequent Ireland-Claisen rearrangement. © The Royal Society of Chemistry 1999.…”

A concise synthesis of the octalactins. by O'Sullivan, P, Buhr, W, Fuhry, M, Harrison, JR, Davies, J, Feeder, N, Marshall, DR, Burton, J, Holmes, AB

“…Key steps include the Paterson-Aldol reaction for the rapid assembly of the carbonate 46, methylenation of 46 and subsequent Claisen rearrangement of the corresponding alkenyl-substituted cyclic ketene acetal to provide the core unsaturated medium-ring lactone 47, and the use of enzyme-mediated acetate deprotection in the presence of a medium-ring lactone.…”

Synthesis of (+)-obtusenyne. by Mak, S, Curtis, N, Payne, A, Congreve, MS, Wildsmith, A, Francis, C, Davies, J, Pascu, S, Burton, J, Holmes, AB

“…An enantioselective synthesis of the halogenated medium-ring ether natural product (+)-obtusenyne is reported which uses the ring expansion of a seven-membered ketene acetal by means of a Claisen rearrangement to construct the core nine-membered oxygen heterocycle. …”