epi-Inositol was synthesized in six steps in 40% overall yield from a bacterial bromobenzene metabolite. The chemoenzymatic route involved toluene dioxygenase oxidation, substrate-directed catalytic osmylation, m-CPBA epoxidation, radical debromination, and Amberlite-catalized hydrolysis. The route described is amenable to scaleup and could allow access to cis-inositol, and deoxy derivatives of epi-inositol.
Vitelio, Cecilia,Bellomo, Ana,Brovetto, Margarita,Seoane, Gustavo,Gonzalez, David
syn-benzene dioxides: Chemoenzymatic synthesis from 2,3-cis-dihydrodiol derivatives of monosubstituted benzenes and their application in the synthesis of regioisomeric 1,2- and 3,4-cis-dihydrodiols and 1,4-dioxocins
cis-2,3-Dihydrodiol metabolites of monosubstituted halobenzenes and toluene have been used as synthetic precursors of the corresponding 3,4-cis-dihydrodiols. Enantiopure syn-benzene dioxide intermediates were reduced to the 3,4-cis-dihydrodiols and therma
Boyd, Derek R.,Sharma, Narain D.,Llamas, Nuria M.,O'Dowd, Colin R.,Allen, Christopher C.R.
p. 2267 - 2273
(2008/03/27)
Enantiopure arene dioxides: Chemoenzymatic synthesis and application in the production of trans-3,4-dihydrodiols
Enantiopure syn- and anti-arene dioxides are synthesised from cis-dihydrodiol metabolites; anti-benzene dioxides are reduced to enantiopure trans-3,4-dihydrodiols while synbenzene dioxides racemise thermally via 1,4-dioxocins.
Boyd,Sharma,O'Dowd,Hempenstall
p. 2151 - 2152
(2007/10/03)
On the dihydroxylation of cyclic allylic alcohols
The preparation and dihydroxylation (OsO4) of a series of conformationally constrained allylic alcohols is described. By using dichloromethane as solvent, the selectivity that favours the anti triol is substantially reduced by hydrogen-bonding
Donohoe, Timothy J.,Garg, Rina,Moore, Peter R.
p. 3407 - 3410
(2007/10/03)
Synthesis of Coduritol D Derivatives from Aromatic Compounds
cis-Cyclohexa-3,5-diene-1,2-diols 3, which are available by microbial oxidation of aromatic compounds, have been converted into 5-substituted conduritols D 5 by catalytic osmylation: application of the emthod to the preparation of homochiral 5-deuteriated
Carless, Howard A. J.,Busia, Kofi,Dove, Yvonne,Malik, Shahnaz S.
p. 2505 - 2506
(2007/10/02)
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