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Divergent Asymmetric Synthesis of Panowamycins, TM-135, and Veramycin F Using C-H Insertion with Donor/Donor Carbenes.
- Source :
- Angewandte Chemie (International ed. in English); vol 61, iss 25, e202203072; 1433-7851
- Publication Year :
- 2022
-
Abstract
- Panowamycins are a group of isochroman-based natural products first isolated from Streptomyces sp. K07-0010 in 2012 by Satoshi Ò„mura and co-workers that exhibit modest anti-trypanosomal activity. Herein we demonstrate the first syntheses of these natural products and their epimers. Stereoselective dirhodium-catalyzed C-H insertion reactions with a donor/donor carbene construct the substituted isochroman core in the key bond-forming step. The syntheses are completed without the use of protecting groups and feature a late-stage Wacker oxidation. Incongruent NMR spectra between natural and synthetic samples revealed the structural misassignment of panowamycin A and veramycin F. Computational NMR studies suggested panowamycin A to be an alternate diastereomer, which was confirmed by synthesizing this isomer. Concurrent with this work, in 2021 Mahmud and co-workers came to the same conclusion with an updated NMR analysis of panowamycin A. In a divergent, asymmetric sequence, we report the synthesis of panowamycin A, panowamycin B, TM-135, and veramycin F.
Details
- Database :
- OAIster
- Journal :
- Angewandte Chemie (International ed. in English); vol 61, iss 25, e202203072; 1433-7851
- Notes :
- application/pdf, Angewandte Chemie (International ed. in English) vol 61, iss 25, e202203072 1433-7851
- Publication Type :
- Electronic Resource
- Accession number :
- edsoai.on1391589601
- Document Type :
- Electronic Resource