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.
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 |
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