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

Organic & Biomolecular Chemistry Pub Date: 2021-10-29 DOI: 10.1039/D1OB02055B

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
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