540462-86-0Relevant academic research and scientific papers
Synthesis of the natural product descurainolide and cyclic peptides from lignin-derived aromatics
Ojo, O. Stephen,Nardone, Brunello,Musolino, Stefania F.,Neal, Andrew R.,Wilson, Liam,Lebl, Tomas,Slawin, Alexandra M. Z.,Cordes, David B.,Taylor, James E.,Naismith, James H.,Smith, Andrew D.,Westwood, Nicholas J.
supporting information, p. 266 - 273 (2018/01/17)
Alternative sources of potential feedstock chemicals are of increasing importance as the availability of oil decreases. The biopolymer lignin is viewed as a source of useful mono-aromatic compounds as exemplified by the industrial scale production of vanillin from this biomass. Alternative lignin-derived aromatics are available in pure form but to date examples of the use of these types of compounds are rare. Here we address this issue by reporting the conversion of an aromatic keto-alcohol to the anti- and syn-isomers of Descurainolide A. The key step involves a rhodium-catalyzed allylic substitution reaction. Enantio-enriched allylic alcohols were generated via an isothiourea-catalyzed kinetic resolution enabling access to both the (2R,3R) and (2S,3S) enantiomers of anti-Descurainolide A. In addition we show that the lignin-derived keto-alcohols can be converted into unnatural amino acid derivatives of tyrosine. Finally, these amino acids were incorporated into cyclic peptide scaffolds through the use of both chemical and an enzyme-mediated macrocylisation.
Synthesis of enantiomerically pure lignin dimer models for catalytic selectivity studies
Njiojob, Costyl N.,Rhinehart, Jennifer L.,Bozell, Joseph J.,Long, Brian K.
, p. 1771 - 1780 (2015/02/19)
A series of highly enantioselective transformations, such as the Sharpless asymmetric epoxidation and Jacobsen hydrolytic kinetic resolution, were utilized to achieve the complete stereoselective synthesis of β-O-4 lignin dimer models containing the S, G, and H subunits with excellent ee (>99%) and moderate to high yields. This unprecedented synthetic method can be exploited for enzymatic, microbial, and chemical investigations into lignins degradation and depolymerization as related to its stereochemical constitution. Preliminary degradation studies using enantiopure Co(salen) catalysts are also reported.
METHOD FOR PREPARING FUROFURAN LIGNAN COMPOUND
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Page/Page column 0028; 0029, (2015/03/16)
The present invention relates to a method for preparing a furofuran lignan compound, comprising a step of selecting and alkylating an epoxy alcohol compound and an optical isomer thereof. (+)-furofuran lignan and (?)-furofuran lignan, as well as an optical isomer thereof, can be selectively prepared by means of the method.
Synthesis of multiply 13C-labeled furofuran lignans using 13C-labeled cinnamyl alcohols as building blocks
Haajanen, Kati,Botting, Nigel P.
, p. 231 - 239 (2007/10/03)
Plant lignans are currently being widely studied for their potential benefits for human health as their consumption has been correlated with lower risks for developing chronic diseases, such as breast cancer and coronary heart disease. However, studies of
