Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Total Synthesis of (−)-Chanoclavine I and an Oxygen-Substituted Ergoline Derivative

Total Synthesis of (−)-Chanoclavine I and an Oxygen-Substituted Ergoline Derivative
Jia-Tian Lu, Zi-Fa Shi, Xiao-Ping Cao
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00573

DOI: 10.1021/acs.joc.7b00573

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