Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 47, Pages 14187-14189Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201508500
Keywords
alkaloids; nitrogen heterocycles; sustainable chemistry; total synthesis; xylochemistry
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Funding
- Carl Zeiss Foundation
- University of Alabama [RG14648]
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The first total synthesis of the dimeric berberine alkaloid ilicifoline (ilicifoline B) is reported. Its carbon skeleton is constructed from ferulic acid, veratrole, and methanol. The synthesis reported herein employs starting materials solely derived from wood. The natural product is thus constructed entirely from renewable resources. The same strategy is applied to a formal total synthesis of morphinan alkaloids. The use of wood-derived building blocks (xylo-chemicals) instead of the conventional petrochemicals represents a sustainable alternative to classical synthetic approaches.
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