Synthesis of the Stenine Ring System from Pyrrole.
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| Title: | Synthesis of the Stenine Ring System from Pyrrole. |
|---|---|
| Authors: | Bates, Roderick W.1 roderick@ntu.edu.sg, Sridhar, S.1 |
| Source: | Journal of Organic Chemistry. 6/17/2011, Vol. 76 Issue 12, p5026-5035. 5p. 5 Charts. |
| Subjects: | Organic field-effect transistors, Ring formation (Chemistry), Chemical reactions, Pyrroles, Chemical reduction, Alkenes |
| Abstract: | The skeleton of the stemona alkaloid, stenine, has been synthesized starting from pyrrole, employing an asymmetric organocatalyzed cyclization, Sonogashira coupling, a diastereoselective intramolecular propargylic Barbier reaction, cyclocarbonylation, and diastereoselective alkene reduction. Modulation of the electron-rich nature of the pyrrole nucleus by employing an α-trifluoroacetyl group is essential. The α-trifluoroacetyl group may be rapidly removed under carefully defined, mild conditions. [ABSTRACT FROM AUTHOR] |
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| Database: | Engineering Source |
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