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
Synthesis of unnatural cyclitols via a combined enzymatic-palladium catalysis approach
Bellomo, Ana,Gonzalez, David,Stefani, Hèlio A.
, p. 1136 - 1142 (2008)
The Suzuki-Miyaura cross-coupling reaction of a hydroxylated vinyl bromide obtained by a chemoenzymatic approach with a diverse range of potassium organotrifluoroborates has been accomplished catalyzed by Pd(PPh3)4 in satisfactory yields. A variety of functional groups are tolerated in the nucleophilic partner.
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,
Antifungal activity of a library of cyclitols and related compounds
Bellomo, Ana,Bertucci, Ana,De La Sovera, Victoria,Carrau, Gonzalo,Raimondi, Marcela,Zacchino, Susana,Stefani, Helio A.,Gonzalez, David
, p. 67 - 75 (2014)
The antifungal activity of a library of 32 cyclitols and derivatives, including 6 previously unreported cyclitol amino acid conjugates, was studied against the clinically important yeasts Candida albicans, Candida tropicalis and Cryptococcus neoformans along with Saccharomyces cerevisiae. Bioautography followed by standardized microbroth dilution methods were used and allowed to identify an azidoinositol glycoside (11) and an azidoconduritol linked to an aromatic aldehyde (18) as promising compounds. The results suggest the relevance of exploring synthetic cyclitolic structures as potential antifungal leaders.
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.
COMPLEMENTARY ENANTIOSPECIFIC SYNTHESES OF CONDURITOL E EPOXIDES FROM HALOBENZENES
Carless, Howard A. J.
, p. 6379 - 6382 (1992)
Microbial oxidation of chlorobenzene and bromobenzene gave diols (3), which were converted in stereoselective and chemoselective sequences involving epoxidation/osmylation steps and reduction to the enantiomers of (-)- or (+)-conduritol E epoxide (4).
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.
Sequential enzymatic and electrochemical functionalization of bromocyclohexadienediols: Application to the synthesis of (?)-conduritol C
Goulart Stollmaier, Juana,Hudlicky, Tomá?
, (2020/01/22)
cis-Diene diol obtained from the microbial oxidation of bromobenzene was used as a substrate for the chemoenzymatic acetylation and epoxidation with lipases. The model studies showed that the regiochemistry of the acetylation is solvent-dependent. The chemoenzymatic epoxidation followed the expected regiochemistry when compared to the chemical epoxidation with m-CPBA, but with the unexpected formation of bromoconduritol-C, an important intermediate whose electrochemical reduction led to the synthesis of (?)-conduritol-C. Experimental and spectral data are provided for all new compounds.
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 Phomentrioloxin A Analogues and Their Evaluation as Herbicidal Agents
Taher, Ehab S.,Guest, Prue,Benton, Amanda,Ma, Xinghua,Banwell, Martin G.,Willis, Anthony C.,Seiser, Tobias,Newton, Trevor W.,Hutzler, Johannes
, p. 211 - 233 (2017/04/26)
A series of 28 analogues of the phytotoxic geranylcyclohexentriol (-)-phomentrioloxin A (1) has been synthesized through cross-couplings of various enantiomerically pure haloconduritols or certain deoxygenated derivatives with either terminal alkynes or borylated alkenes. Some of these analogues display modest herbicidal activities, and physiological profiling studies suggest that analogue 4 inhibits photosystem II in isolated thylakoids in vitro.