Total Synthesis of (-)-Chanoclavine I and an Oxygen-Substituted Ergoline Derivative.
| Autor: | Lu JT; State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou 730000, P. R. China., Shi ZF; State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou 730000, P. R. China., Cao XP; State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou 730000, P. R. China. |
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| Jazyk: | angličtina |
| Zdroj: | The Journal of organic chemistry [J Org Chem] 2017 Aug 04; Vol. 82 (15), pp. 7774-7782. Date of Electronic Publication: 2017 Jul 17. |
| DOI: | 10.1021/acs.joc.7b00573 |
| Abstrakt: | An efficient and direct route to ergot alkaloid (-)-chanoclavine I (3) is described using the inexpensive compound (2R)-(+)-phenyloxirane (15) as a chiral pool in 13 steps with 17% overall yield. Key features of the synthesis include a palladium-catalyzed intramolecular aminoalkynylation of terminal olefin and a rhodium-catalyzed intramolecular [3 + 2] annulation. An oxygen-substituted ergoline derivative (-)-25 was also achieved by using the same strategy. |
| Databáze: | MEDLINE |
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