Synthesis of Functionalized δ-Hydroxy-β-keto Esters and Evaluation of Their Anti-inflammatory Properties

Description

δ-Hydroxy-β-keto esters and δ,β-dihydroxy esters are characteristic
structural motifs of statin-type natural products and drug
candidates. Here, we describe the synthesis of functionalized δ-
hydroxy-β-keto esters in good yields and excellent enantioselectivities
using Chan’s diene and modified Mukaiyama-aldol
reaction conditions. Diastereoselective reduction of δ,β-dihydroxy
esters afforded the respective syn- and anti-diols, and
saponification yielded the corresponding acids. All products
were evaluated for their anti-inflammatory properties, which
uncovered a surprising structure-activity relationship.

Links & Downloads

1. urn:nbn:de:bsz:15-qucosa2-866197
2. https://ul.qucosa.de/id/qucosa%3A86619
3. https://ul.qucosa.de/api/qucosa%3A86619/attachment/ATT-0/

Tags

δ-Hydroxy-β-keto Esters, Synthesis

info:eu-repo/classification/ddc/540

ddc:540

Additional Fields

Identifer	oai:union.ndltd.org:DRESDEN/oai:qucosa:de:qucosa:86619
Date	27 July 2023
Creators	Grosse, Michel, Günther, Kerstin, Jordan, Paul M., Roman, Dávid, Werz, Oliver, Beemelmanns, Christine
Publisher	Wiley-VCH
Source Sets	Hochschulschriftenserver (HSSS) der SLUB Dresden
Language	English
Detected Language	English
Type	info:eu-repo/semantics/publishedVersion, doc-type:article, info:eu-repo/semantics/article, doc-type:Text
Rights	info:eu-repo/semantics/openAccess
Relation	1439-7633, e202200073