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Diastereoselective synthesis of the -decalin-based α-hydroxyl butanone spirocarbocycles bearing all-carbon quaternary stereogenic centers has been achieved via Norrish-Yang photocyclization of -decalin-substituted-2,3-butanediones using daylight. Density functional theory (DFT) calculations suggest that this diastereoselective reaction is affected by both substrate conformation and intramolecular hydrogen bonds. The developed chemistry could be applied to synthesizing the derivatives of the -decalin-based biologically important natural products.
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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8320103 | PMC |
http://dx.doi.org/10.1021/acsomega.1c02054 | DOI Listing |
J Med Chem
January 2020
Institute for Organic Chemistry and Biochemistry , Technische Universität Darmstadt, Alarich-Weiss-Strasse 4 , D-64287 Darmstadt , Germany.
Selective inhibition of FKBP51 has emerged as possible novel treatment for diseases like major depressive disorder, obesity, chronic pain, and certain cancers. The current FKBP51 inhibitors are rather large, flexible, and have to be further optimized. By using a structure-based rigidification strategy, we hereby report the design and synthesis of a novel promising bicyclic scaffold for FKBP51 ligands.
View Article and Find Full Text PDFOrg Biomol Chem
May 2005
Department of Chemistry, Imperial College, South Kensington campus, London, UK SW7 2AZ.
The syntheses of three decalin-based tert-thiols displaying varying degrees of solubility in aqueous milieu are described. The S-nitroso derivatives of these compounds have also been prepared and the structures of two of these determined by single crystal X-ray diffraction. These compounds have been designed for studying the interaction of nitric oxide (NO) with thiols under physiological conditions.
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