A short synthesis of (±)-tecomanine via a Pauson-Khand-based route

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The N-carboethoxy precursor to (±)-tecomanine has been prepared in 11 steps from 2-methyl-1-buten-3-yne. The key step, Pauson-Khand cyclization of a methylated 5-aza-6-nonen-1-yne succeeds, but only in low yield, a consequence of the dialkyl substitution about the azaenyne framework. Nevertheless, the overall sequence to that point is one of the more efficient to be described. © 2003 Elsevier Science Ltd. All rights reserved.




Ockey, D. A., Lewis, M. A., & Schore, N. E. (2003). A short synthesis of (±)-tecomanine via a Pauson-Khand-based route. Tetrahedron, 59(28), 5377–5381. https://doi.org/10.1016/S0040-4020(03)00779-8

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