| Autor: |
Vargas, Didier F., Romero, Brenda S., Larghi, Enrique L., Kaufman, Teodoro S. |
| Předmět: |
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| Zdroj: |
Synthesis; 2020, Vol. 52 Issue 1, p119-126, 8p |
| Abstrakt: |
The concise and efficient first total synthesis of 6- O -methyl anciscochine, employing a tandem C–C/C–N formation approach via a rhodium-catalyzed C–H activation/alkenylation/annulation strategy, is reported. This heterocycle was isolated from the liana Ancystrocladus tectorius and features a unique 3-hydroxymethylisoquinoline core that is found in a few other natural products and in some bioactive synthetic compounds. The synthesis, which was executed in four high-yielding steps and a global yield of 43%, involved the oximation of commercial 2,4-dimethoxyacetophenone under CeCl3 ·7H2 O-promotion, followed by pivaloylation of the oxime. A one-pot pivaloxime-directed alkenyl-ation/annulation stage with methyl acrylate, furthered by a NaBH4 / CaCl2--mediated reduction of the resulting isoquinoline 3-carboxylate ester completed the sequence. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
| Externí odkaz: |
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