Journal article
Comparative Study of the Kumada, Negishi, Stille, and Suzuki-Miyaura Reactions in the Synthesis of the Indole Alkaloids Hippadine and Pratosine
In
Journal of Organic Chemistry
—
2006, Volume 71, Issue 15, pp. 5807-5810
Abstract
The total synthesis of hippadine by a tandem metalation/cross-coupling/lactamization strategy was investigated starting from either 7-bromoindole or a 6-halogenated methyl piperonate. The Kumada and Negishi cross-coupling reactions failed to provide any of the desired product. However, the Stille and Suzuki reactions furnished hippadine in low yields starting from the electron-deficient methyl 6-iodo- and 6-bromopiperonate, respectively.
Starting from the metalated indole, only the Suzuki reaction occurred, affording hippadine in 67-74% and pratosine in 62% isolated yield.
| Language: | English |
|---|---|
| Year: | 2006 |
| Pages: | 5807-5810 |
| ISSN: | 15206904 and 00223263 |
| Types: | Journal article |
| DOI: | 10.1021/jo060729b |
| ORCIDs: | Tanner, David Ackland |
