| Autor: |
Russell DA; Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK. spring@ch.cam.ac.uk., Freudenreich JJ, Stewart HL, Bond AD, Sore HF, Spring DR |
| Jazyk: |
angličtina |
| Zdroj: |
Organic & biomolecular chemistry [Org Biomol Chem] 2018 Sep 11; Vol. 16 (35), pp. 6395-6398. |
| DOI: |
10.1039/c8ob01919c |
| Abstrakt: |
We describe semi-syntheses of the 11-hydroxyrotenoids sumatrol (1) and villosinol (2), starting from rotenone (5), using an oxime-directed C11-H functionalisation approach. Thus, rotenone (5) was converted into rotenone oxime (6), which gave dimeric palladacycle 7 following reaction with Na2PdCl4·3H2O. Controlled, divergent, oxidation of palladacycle 7 with either Pb(OAc)4 or K2Cr2O7 afforded the 11-acetoxylated intermediates 9 and 13, respectively, which were transformed into sumatrol (1) and villosinol (2). |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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