A biomimetic synthesis-enabled stereochemical assignment of rhodotomentones A and B, two unusual caryophyllene-derived meroterpenoids from Rhodomyrtus tomentosa
Literature Information
Publication Date
2021-08-19
DOI
10.1039/D1QO00989C
Impact Factor
5.281
Authors
Yue-Yue Li, Yao-Lan Li
View Original
Abstract
Rhodotomentones A and B (1 and 2), two unusual caryophyllene-derived meroterpenoids (CDMTs) featuring a rare 6/6/9/4/6/6 hexacyclic ring system, along with their biogenetically-related CDMTs 7 and 12–15, were isolated from Rhodomyrtus tomentosa. The planar structures of 1 and 2 were established by comprehensive spectroscopic data analyses. Based on their unique structural features, compounds 1 and 2 were hypothesized to be biosynthesized from three different building blocks. Inspired by two potentially biogenetic pathways, we completed the biosynthetic building block-based syntheses of 1 and 2, which enabled the unambiguous stereochemical assignment of 1 and 2. In addition, three CDMTs 10, 14, and 17 exhibited potent in vitro antiviral activities against respiratory syncytial virus (RSV).
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
1-(3-Bromophenyl)-4-oxocyclohexanecarboxylic acid
CAS Number:
1385694-53-0
Molecular Formula:
C13H13BrO3
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