Simple chemoenzymatic access to enantiopure pharmacologically interesting (R)-2-hydroxypropiophenones

Date

2001-07-30

Author

Demir, AS
Hamamcı, Haluk
Sesenoglu, O
Aydogan, F
Capanoglu, D
Neslihanoglu, R

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

125
views

0
downloads

A chemoenzymatic synthesis of pharmacological interesting (R)-2-hydroxypropiophenones starting from propiophenone derivatives is described. Manganese(III) acetate-mediated acetoxylation followed by fungus-mediated hydrolysis of propiophenone derivatives affords (R)-2-hydroxypropiophenones in high enantiomeric excess.

Subject Keywords

Alpha-hydroxy ketones, Enantioselective synthesis, Benzoylformate decarboxylase, Antifungals, Derivatives, Resolution, Precursor, Oxidation, Acetoxy, Salts

URI

https://hdl.handle.net/11511/30861

Journal

TETRAHEDRON-ASYMMETRY

DOI

https://doi.org/10.1016/s0957-4166(01)00346-9

Collections

Graduate School of Natural and Applied Sciences, Article

Suggestions

OpenMETU
Core

Synthesis and biological evaluation of optically active conjugated gamma- and delta-lactone derivatives ŞARDAN, Melis; Sezer, Serdar; GUNEL, Aslihan; AKKAYA, MAHİNUR; Tanyeli, Cihangir (2012-09-15) An efficient synthesis of racemic and both enantiomeric forms of heteroaryl substituted gamma- and delta-lactone derivatives derived from allyl and homoallyl alcohol backbones has been accomplished via ring closing metathesis reaction. 2-Heteroaryl substituted allyl and homoallyl alcohols have been efficiently resolved through enzymatic method with high ee (97-99%) and known stereochemistry. Antimicrobial and antioxidant activities of target lactones were evaluated.
A new and efficient chemoenzymatic route to both enantiomers of alpha '-acetoxy and alpha '-hydroxy-alpha-methoxy cyclic enones Demir, Ayhan Sıtkı; Caliskan, Z; Aydin, AE; Bicer, I (Elsevier BV, 2006-03-06) A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy and alpha'-hydroxy-alpha-methoxy cyclic enones starting from alpha-hydroxy cyclic enones is described. Protection of 1,2-diketones, manganese(III) acetate-mediated acetoxylation followed by enzyme-mediated hydrolysis of alpha'-acetoxy enones gives acetoxy enones 3a-d and hydroxy enones 4a-d with high enantiomeric excesses (up to 99%) and good yields. The transesterification of rac-4b in the presence of DMAP af...
Auxiliary mediated synthesis of aziridine 2 carboxylic acid derivative GARNER, Philip; Doğan, Özdemir; PİLLAİ, Satish (1994-03-01) A convenient protocol for the asymmetric synthesis of stereodefined aziridine-2-carboxylic acid derivatives from alpha,beta-unsaturated acryloyl- and crotonoyl camphor sultams is reported.
Stereoselective synthesis of gamma-lactone fused cyclopentanoids Gumus, Aysegul; Tanyeli, Cihangir (2012-10-15) The stereoselective synthesis of gamma-lactone fused cyclopentanoids applying chemoenzymatic methods is described. rac-2-Hydroxymethyl-1,4,5,6-tetrachloro-7,7-dimethoxybicyclo[2.2.1]hept-5-ene and rac-2-hydroxymethyl-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene were successfully resolved by Candida rugosa lipase (CRL), to afford enantiomerically enriched products with an ee of 94 and 97%, respectively. The enantiomerically enriched acetates were then subjected to ruthenium and/or cerium catalyzed oxidatio...
Synthesis of Bishomoinositols and an Entry for Construction of a Substituted 3-Oxabicyclo[3.3.1]nonane Skeleton BARAN, ARİF; Bekarlar, Merve; Aydin, Gokay; NEBİOĞLU, MEHMET; ŞAHİN, Ertan; Balcı, Metin (2012-02-03) 1,3,3a,7a-Tetrahydro-2-benzofuran was used as key compound for the synthesis of various bishomoinositol derivatives. The diene was subjected to an epoxidation reaction for further functionalization of the diene unit. The bisepoxide obtained was submitted to a ring-opening reaction with acid in the presence of water. Various bishomoinositols were synthesized. However, when the reaction was carried out in the presence of acetic anhydride, a substituted 3-oxabicyclo[3.3.1]nonane skeleton was formed. The mechan...

Citation Formats

A. Demir, H. Hamamcı, O. Sesenoglu, F. Aydogan, D. Capanoglu, and R. Neslihanoglu, “Simple chemoenzymatic access to enantiopure pharmacologically interesting (R)-2-hydroxypropiophenones,” TETRAHEDRON-ASYMMETRY, pp. 1953–1956, 2001, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/30861.