Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 19, Issue 45, Pages 9840-9843Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ob02055b
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Funding
- National Natural Science Foundation of China [21772078, 22071200]
- Science and Technology Department of Sichuan Province [2020JDRC0021]
- Fundamental Research Funds for the Central Universities [2682020CX55, 2682021ZTPY011, XJ2021KJZK004]
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The first total synthesis of (+)-adunctin C and (+)-adunctin D, two monoterpene-substitued dihydrochalcones isolated from Piper aduncum, was achieved through a regioselective oxidative [3 + 2] cycloaddition of acylphloroglucinol with (-)-beta-phellandrene to construct their unique spiro-benzofuran skeleton. This allowed for the assignment of the absolute configurations of natural adunctins 1 and 2.
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 (-)-beta-phellandrene was developed to construct their unique spiro-benzofuran skeleton. The absolute configurations of natural adunctins 1 and 2 were thus assigned through these endeavors.
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