Synthesis of the Dimeric Diarylheptanoids Alpinidinoid C and Officinine B Enabled by Blue-Light-Mediated Triple-Minisci-Type Alkylation.

Autor: Schultz DC; Warren Center for Neuroscience Drug Discovery and Department of Pharmacology, Vanderbilt University, Nashville, Tennessee 37232, United States., Rathnayake U; Warren Center for Neuroscience Drug Discovery and Department of Pharmacology, Vanderbilt University, Nashville, Tennessee 37232, United States., Duncan RA; Warren Center for Neuroscience Drug Discovery and Department of Pharmacology, Vanderbilt University, Nashville, Tennessee 37232, United States., Richardson AE; Warren Center for Neuroscience Drug Discovery and Department of Pharmacology, Vanderbilt University, Nashville, Tennessee 37232, United States., Bender AM; Warren Center for Neuroscience Drug Discovery and Department of Pharmacology, Vanderbilt University, Nashville, Tennessee 37232, United States.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2024 Oct 25; Vol. 26 (42), pp. 9028-9033. Date of Electronic Publication: 2024 Oct 10.
DOI: 10.1021/acs.orglett.4c03227
Abstrakt: The first syntheses of the Alpinia officinarum natural products alpinidinoid C and officinine B are reported. These unusual dimeric diarylheptanoids were accessed from a 3-substituted pyridine intermediate via a blue-light-mediated, triple-Minisci-type alkylation. Very few reports utilize N -(acyloxy)phthalimides (NAPs) in the construction of natural products, and the syntheses reported herein highlight the power of this methodology toward the orthogonal construction of highly substituted arenes.
Databáze: MEDLINE