Issue 23, 2021

Total syntheses of melodienones by redox isomerization of propargylic alcohols

Abstract

A remarkable base-promoted methodology for the rapid construction of the (E)- and (Z)-γ-oxo-α,β-alkenoic ester skeletons from readily accessible vinyl propargylic alcohols through modified redox isomerization was uncovered. This approach manifested its high simplicity and efficiency with excellent tolerance of functional substituents, which led to the straightforward structural modifications of various natural products and efficient total syntheses of melodienone, homomelodienone, isomelodienone, and homoisomelodienone within 4 linear steps.

Graphical abstract: Total syntheses of melodienones by redox isomerization of propargylic alcohols

Supplementary files

Article information

Article type
Communication
Submitted
29 mar 2021
Accepted
14 may 2021
First published
20 may 2021

Org. Biomol. Chem., 2021,19, 5077-5081

Total syntheses of melodienones by redox isomerization of propargylic alcohols

C. Dong, W. Peng, H. Wang, X. Zhang, J. Zhang, G. Tan, K. Xu, Z. Zou and H. Tan, Org. Biomol. Chem., 2021, 19, 5077 DOI: 10.1039/D1OB00599E

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