52183-77-4Relevant academic research and scientific papers
REACTIVITY STUDIES IN THE SHIKIMIC ACID SERIES: THE SYNTHESIS OF RACEMIC METHYL 6α-FLUOROSHIKIMATE
Bowles, Stephen A.,Campbell, Malcolm M.,Sainsbury, Malcolm,Davies, Gareth M.
, p. 3981 - 3992 (2007/10/02)
The regio- and stereo-selective epoxidation of methyl 3,4-dihydrobenzoate derivatives has been investigated.Perbenzimidic acid leads only to epoxides formed at the Δ1,2 bond.More electrophilic reagents such as MCPBA also give products of this t
REACTIVITY STUDIES IN THE SHIKIMIC ACID SERIES
Bowles, Stephen,Campbell, Malcolm M.,Sainsbury, Malcolm,Davies, Gareth M.
, p. 3711 - 3714 (2007/10/02)
The regio- and stereo-selective epoxidation of methyl 3,4-dihydrobenzoate has been investigated and a synthesis of racemic methyl 6α-fluoroshikimate from the acetonide of methyl 3,4-dihydro-3α,4α-cyclohexenoate is described.This work has importance for th
BRIEF SYNTHESES OF (+/-)-METHYL SHIKIMATE, (+/-)-METHYL EPISHIKIMATE AND STRUCTURAL VARIANTS
Campbell, Malcolm M.,Kaye, Aston D.,Sainsbury, Malcolm,Yavarzadeh, Roya
, p. 2461 - 2470 (2007/10/02)
Two brief syntheses of (+/-)-methyl shikimate are described in a strategy which offers potentially flexible access to a range of analogues.New intramolecular rearrangement reactions of epoxides derived from methyl 7-oxabicyclohept-3-ene 6-carboxylate and methyl bicyclohept-3-ene 6 carboxylate are described.
BRIEF DIELS ALDER SYNTHESIS OF (+/-)-METHYL 5-EPISHIKIMATE AND (+/-)-METHYL CIS-3,4-DIHYDRO-3,4-DIHYDROXYBENZOATE
Campbell, Malcolm M.,Kaye, Aston D.,Sainsbury, Malcolm
, p. 4745 - 4746 (2007/10/02)
Base-catalysed ring opening of the acetonide of cis-exo-2,3-dihydroxy-6-methoxycarbonyl-7-oxabicycloheptane affords a stereo-controlled route to (+/-)-methyl 5-epishikimate and thence, by an elimination process, to (+/-)-methyl-cis-3,4-dihydro-3,4-dihydroxybenzoate.
