Lipase-catalysed regio- and enantioselective deacetylation of 2,4-diacetoxyphenyl alkyl ketones

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

“…This type of olefination of ortho-hydroxycarbonyl aromatic compounds, followed by further lactonisation, is a well-known method for the preparation of coumarin derivatives [9,108,122,[144][145][146][147][148][149] other type of coumarin derivatives (Scheme 8) [96,[158][159][160]. These coumarins are suitable starting materials for obtaining another type of compounds such as styril and acetyl derivatives, hydrazones, etc.…”

Enzymatic Protecting Group Techniques

“…In addition, aryl alkyl ketones which are important starting materials for the synthesis of polyphenolic natural products may be manipulated selectively by making use of an enzymatic saponification. ,− In general, in these cases the sterically more accessible ester groups are cleaved, as, for instance, in 185 . All of these examples have in common that a carbonyl group is either directly or vinylogously attached to the aryl moiety.…”

Synthesis of macromolecular systems via lipase catalyzed biocatalytic reactions: applications and future perspectives

“…2). [10][11][12][13][14][15][16][17][18][19] Selective deacetylations were studied on these substrates and it was observed that while using porcine pancreatic lipase (PPL), selective deacetylation occurred at the para-and metapositions with reference to the nuclear carbonyl group, in comparison to that at the ortho-acetoxy group. These results were found to be important and interesting as an ortho-acetoxy moiety would preferentially undergo deacetylation under chemical conditions due to chelation of the resulting hydroxyl group with the carbonyl group.…”

“…79 Similarly, enzyme catalyzed condensation polymerization using adipic acid, hexane diol and other bi-functional building blocks have been successfully reported, 80,81 further progress in this area focused mainly on designing functional diols or diacids, which offers flexibility for post-modification to conjugate bio-active molecules. 82 Our vast experience of enzymatic transformations on small molecules [10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][33][34][35]39,[42][43][44][45][47][48][49] has allowed us to utilize these extremely efficient and selective biocatalysts on customized monomers for synthesizing polymers and polymeric amphiphiles that aggregate to form nanospheres for various applications. Our efforts primarily focused on synthesizing polyethylene glycol (PEG) based block copolymers considering the biocompatibility of these polymers for biomedical applications.…”