130669-74-8Relevant articles and documents
New, homochiral synthons obtained through simple manipulations of enzymatically derived 3-halo-cis-1,2-dihydrocatechols
White, Lorenzo V.,Lan, Ping,Schwartz, Brett D.,Willis, Anthony C.,Banwell, Martin G.
, p. 1467 - 1471 (2015)
The bromoepoxide 5a, which is obtained from the homochiral and enzymatically derived cis-1,2-dihydrocatechol 1a, is readily and efficiently transformed into either isomer 8a or the corresponding methoxymethyl-ether 2a. Though both of these products can be
Selectivity in the halohydroxylation of cyclohexadienediols
Carrera, Ignacio,Brovetto, Margarita C.,Seoane, Gustavo
, p. 4095 - 4107 (2007)
The halohydroxylation of a number of cyclohexadienediol derivatives has been investigated. The selectivity of the reaction as a function of the type of substituent on the diene, protecting group of the diol functionality, halonium donor, medium polarity,
Synthesis of the enantiomer of the structure assigned to the natural product nobilisitine A
Schwartz, Brett D.,Jones, Matthew T.,Banwell, Martin G.,Cade, Ian A.
, p. 5210 - 5213 (2010)
The synthesis of the enantiomer of the structure, 1, assigned to the natural product nobilisitine A has been accomplished using the enantiomerically pure cis-1,2-dihydrocatechol 4 as starting material. The 1H and 13C NMR spectral data derived from compound ent-1 do not match those reported for the natural product, thus suggesting its structure has been incorrectly assigned.
Readily accessible azido-alkyne-functionalized monomers for the synthesis of cyclodextrin analogues using click chemistry
Daher, Grysette,Seoane, Gustavo
supporting information, p. 1690 - 1698 (2022/03/02)
A set of linear and cyclic oligomers were synthesized starting from a suitable azido-alkyne monomer through click oligomerization. The synthesis of these monomers starting from bromobenzene features an enzymatic dihydroxylation and the regio- and stereoselective installation of the azide and alkyne functionalities. Optimization of the click reaction was accomplished using dimerization as the model reaction. The product distribution of the oligomerization could be modulated by the monomer concentration and the use of additives, generating mainly cyclic oligomers consisting of tetramers, pentamers and hexamers.
Chemoenzymatic synthesis of hygromycin aminocyclitol moiety and its C2 epimer
Carrau, Gonzalo,Bellomo, Ana Inés,Suescun, Leopoldo,Gonzalez, David
, p. 788 - 802 (2019/01/08)
This manuscript describes the enantioselective synthesis of the aminocyclitol moiety of the antibiotic hygromycin A in eight steps and 39 % overall yield from a non-chiral starting material. The sequence made use of an initial enzymatic step to transfer chirality to an aromatic ring and was followed by selective organic chemistry transformations (oxidation, pro-tection, azidation, hydrolysis) of the six-membered ring in order to achieve the target. The approach is also amenable to the synthesis of other related unnatural analogues as exemplified by the synthesis of the C2 epimer of the natural aminocyclitol. All the intermediates were fully characterized, and the absolute stereochemistry assigned by spectrometric methods.
The Synthesis of Certain Derivatives and Analogues of (-)- and (+)-Galanthamine and an Assessment of their Capacities to Inhibit Acetylcholine Esterase
Buckler, Joshua N.,Taher, Ehab S.,Fraser, Nicolas J.,Willis, Anthony C.,Carr, Paul D.,Jackson, Colin J.,Banwell, Martin G.
, p. 7869 - 7886 (2017/08/14)
Syntheses of certain di- and mono-oxygenated derivatives (e.g., 2 and 3, respectively) and analogues (e.g., 4, a D-ring monoseco-analogue of 2) of both the (-)- and (+)-enantiomeric forms of the alkaloid galanthamine [(-)-1] are reported. All have been assessed for their capacities to inhibit acetylcholine esterase but, in contrast to the predictions from docking studies, none bind strongly to this enzyme.