Stereochemical revision of brevipetins E and F: ellagitannin dimers with opposite hexahydroxydiphenoyl atropisomerism
Brevipetins E and F, ellagitannin dimers from <i>Cleidion brevipetiolatum</i>, were originally reported to bear both a 3,4-(<i>R</i><sub>a</sub>)-hexahydroxydiphenoyl (HHDP)-glucopyranose and a 3,4-(<i>R</i><sub>a</sub>)-HHDP-rhamnopyranose moiety. However, a detailed reevaluation of the reported electronic circular dichroism (ECD) data, corroborated by DFT-based <sup>1</sup>H and <sup>13</sup>C NMR chemical shift and ECD calculations, supports a stereochemical reassignment of these ellagitannins. Accordingly, the 3,4-HHDP-rhamnopyranose moiety in these compounds is reassigned to the (<i>S</i><sub>a</sub>)-atropisomeric configuration, in line with the observed reduction in Δ<i>ε</i> magnitudes relative to the constituent monomers.
Authors
- Yosuke Matsuo (ORCID: https://orcid.org/0000-0002-6462-9727)
- Yoshinori Saito (ORCID: https://orcid.org/0000-0002-3587-9743)
- Ryo Ohtsuka
- Fumika Yakushiji (ORCID: https://orcid.org/0000-0002-9003-3767)
- Takashi Tanaka (ORCID: https://orcid.org/0000-0001-7762-7432)
- Koji Yamada (ORCID: https://orcid.org/0000-0002-5084-7571)
Institutions
- Nagasaki University (JP)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ob01323b
- Citations
- 1
- Primary Topic
- Axial and Atropisomeric Chirality Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.94