Journal
TETRAHEDRON LETTERS
Volume 61, Issue 47, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2020.152538
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Funding
- Japan Society for the Promotion of Science
- New Zealand Government
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Dihydrolevoglucosenone (DLGO) and amino aldehydes undergo an aldol reaction mediated by the heterogenous base KF-alumina; exposure of the aldol adducts to hydrogenation followed by silica gel results in the formation of pyrrole-2-carbaldehydes bearing the jiangrine alkaloid scaffold. KF-alumina is also an effective base in the aldol condensation between DLGO and aliphatic/aromatic aldehydes, with no self-aldol reaction apparent. (C) 2020 Elsevier Ltd. All rights reserved.
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