| Autor: |
Singh A; Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India., Kaliappan KP; Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India. |
| Jazyk: |
angličtina |
| Zdroj: |
The Journal of organic chemistry [J Org Chem] 2024 Aug 02; Vol. 89 (15), pp. 10965-10973. Date of Electronic Publication: 2024 Jul 22. |
| DOI: |
10.1021/acs.joc.4c01393 |
| Abstrakt: |
Herein, we report the first asymmetric total synthesis of 4-hydroxy-8- O -methyltetrangomycin ( 1 ), 4-hydroxytetrangomycin ( 2 ), and 4-keto-8- O -methyltetrangomycin ( 3 ), angucyclinones featuring a highly oxidized nonaromatic A ring. A sequential enyne metathesis/Diels-Alder approach was utilized successfully to construct the tetracyclic skeleton of the angucyclinones. Late-stage acetonide deprotection challenges were overcome by A ring functional group manipulation, yielding a dihydroxy intermediate prior to the benzylic photo-oxidation, facilitating the total syntheses of angucyclinones 1 - 3 . The key stereocenter was established through a known Sharpless asymmetric epoxidation/regioselective epoxide opening reaction. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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