Journal
TETRAHEDRON LETTERS
Volume 52, Issue 44, Pages 5744-5746Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.08.050
Keywords
(-)-Funebrine; Au-catalyzed lactonization; Allenylsilane; gamma-Butyrolactone; Paal-Knorr pyrrole condensation
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Funding
- Japan Society of the Promotion of Science (JSPS) [16201045, 19201045]
- Grants-in-Aid for Scientific Research [23102009, 21310145, 19201045] Funding Source: KAKEN
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The stereoselective total synthesis of (-)-funebrine from 2-butyn-1-ol was described. The crucial steps in the synthesis involved the stereoselective enolate Claisen rearrangement of the (S)-alpha-acyloxy-alpha-alkynylsilane 8, the Au-catalyzed regio- and stereoselective lactonization of the allenylsilane 7, and the Paal-Knorr pyrrole condensation using an unsymmetrical 1,4-diketone 4b. (C) 2011 Elsevier Ltd. All rights reserved.
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