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One-Pot Tandem Aldol-Cycloetherification Protocol in the Enantioselective Synthesis of Davanoids by Vipin Kumar Singh; Jothi Lakshmi Nallasivam; Tushar Kanti Chakraborty is a Chemistry article available to read on EtoBox.

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Total synthesis of cis and trans diastereomers of prenylated davanoids like davanone, nordavanone, and davana acid ethyl ester was achieved in an enantioselective strategy. Various other davanoids could also be synthesized using standard procedures from the Weinreb amides derived from davana acids. Enantioselectivity in our synthesis was achieved employing a Crimmins' non-Evans syn aldol reaction that fixed the stereochemistry of the C3-hydroxyl group, while the C2-methyl group was epimerized in a late stage of the synthesis. A Lewis acidmediated cycloetherification reaction was used to establish the tetrahydrofuran core of these molecules. Interestingly, a slight alteration of the Crimmins' non-Evans syn aldol protocol led to the complete conversion of the aldol adduct to the core tetrahydrofuran ring of davanoids, thus essentially dovetailing two important steps in the synthesis. The resulting one-pot tandem aldol-cycloetherification strategy enabled the enantioselective synthesis of trans davana acid ethyl esters and 2-epi-davanone/ nordavanone in just three steps in excellent overall yields. The modularity of the approach will enable the synthesis of various other isomers in st

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Author

Vipin Kumar Singh; Jothi Lakshmi Nallasivam; Tushar Kanti Chakraborty

Publisher

American Chemical Society (ACS)

Published

2023

Language

EN

Field

Chemistry (Physical Sciences)