Issue 45, 2021

Total syntheses of (+)-adunctins C and D: assignment of their absolute configurations

Abstract

The first total synthesis of (+)-adunctin C (ent-1) and (+)-adunctin D (2), two monoterpene-substitued dihydrochalcones isolated from Piper aduncum (Piperaceae), was achieved. A regioselective oxidative [3 + 2] cycloaddition of acylphloroglucinol with (−)-β-phellandrene was developed to construct their unique spirobenzofuran skeleton. The absolute configurations of natural adunctins 1 and 2 were thus assigned through these endeavors.

Graphical abstract: Total syntheses of (+)-adunctins C and D: assignment of their absolute configurations

Supplementary files

Article information

Article type
Communication
Submitted
19 oct. 2021
Accepted
29 oct. 2021
First published
29 oct. 2021

Org. Biomol. Chem., 2021,19, 9840-9843

Total syntheses of (+)-adunctins C and D: assignment of their absolute configurations

J. Xiao, J. Zhao, Y. Wang, G. Luo and Y. Peng, Org. Biomol. Chem., 2021, 19, 9840 DOI: 10.1039/D1OB02055B

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