A Xylochemically Inspired Synthesis of Lamellarin G Trimethyl Ether via an Enaminone Intermediate

A Xylochemically Inspired Synthesis of Lamellarin G Trimethyl Ether via an Enaminone Intermediate

A concise high yielding synthesis of lamellarin G trimethyl ether has been achieved from precursors and solvents that can in principle be derived from xylochemical (woody biomass) sources. The route is comparatively green in that some reactions are performed without solvent or with relatively benign...

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Veröffentlicht in:Journal of organic chemistry 2019-09, Vol.84 (17), p.11025-11031
Hauptverfasser: Klintworth, Robin, de Koning, Charles B, Opatz, Till, Michael, Joseph P
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container_end_page 11031
container_issue 17
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container_title Journal of organic chemistry
container_volume 84
creator Klintworth, Robin
de Koning, Charles B
Opatz, Till
Michael, Joseph P
description A concise high yielding synthesis of lamellarin G trimethyl ether has been achieved from precursors and solvents that can in principle be derived from xylochemical (woody biomass) sources. The route is comparatively green in that some reactions are performed without solvent or with relatively benign solvents. In addition, chromatographic purification of products is avoided, and only a single aqueous workup is performed. The novelty of the synthesis lies in the intermediacy of an enaminone for the construction of the central pyrrole ring. The overall yield of the product is among the highest reported to date.
doi_str_mv 10.1021/acs.joc.9b01604
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title A Xylochemically Inspired Synthesis of Lamellarin G Trimethyl Ether via an Enaminone Intermediate
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