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Asymmetric Total Synthesis of (+)-Hyperbeanol A.
Org Lett
January 2025
State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
A bioinspired alkylation dearomatization reaction was developed to construct the 5/6/6 fused-spiro tricyclic core framework and spiro-quaternary carbon chiral center. The usage of this approach for assembling these natural products of spirocyclic polycyclic polyprenylated acylphloroglucinols with an octahydrospiro-[cyclohexan-1,5'-indene] core is demonstrated by the first asymmetric total synthesis of highly oxidized hyperbeanol A.
View Article and Find Full Text PDFIsolation and Biomimetic Semisynthesis of Hyperzrones A and B, Two Nor-Polycyclic Polyprenylated Acylphloroglucinols with a Characteristic Cyclobutane Moiety, from .
Org Lett
December 2024
Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 210009, People's Republic of China.
Article Synopsis
- Two new compounds, Hyperzrones A and B, are unique polycyclic polyprenylated acylphloroglucinols with a cyclobutane structure.
- Their structures were confirmed using a combination of spectroscopic analysis, X-ray crystallography, and quantum chemical calculations.
- A bioinspired method was developed to synthesize these compounds from hypercalin B, along with creating various derivatives for further biological research.
Polycyclic Polyprenylated Acylphloroglucinols (PPAPs) from Garcinia Oblongifolia and their Antitumor Activity.
Chem Biodivers
October 2024
State Key Laboratory of Bioactive Molecules and Druggability Assessment, and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM & New Drugs Research College of Pharmacy, Jinan University, Guangzhou, 510632, P. R. China.
Article Synopsis
- Two new compounds, along with four known ones, were discovered in the fruits of Garcinia oblongifolia.
- The structures of these compounds were determined using various methods, such as mass spectrometry and NMR.
- Compounds 1 and 2 showed potential as cancer-fighting agents in tests against a specific cell line.
Catalytic prenyl conjugate additions for synthesis of enantiomerically enriched PPAPs.
Science
October 2024
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467, USA.
Polycyclic polyprenylated acylphloroglucinols (PPAPs) are a class of >400 natural products with a broad spectrum of bioactivity, ranging from antidepressant and antimicrobial to anti-obesity and anticancer activity. Here, we present a scalable, regio-, site-, and enantioselective catalytic method for synthesis of cyclic β-prenyl ketones, compounds that can be used for efficient syntheses of many PPAPs in high enantiomeric purity. The transformation is prenyl conjugate addition to cyclic β-ketoesters promoted by a readily accessible chiral copper catalyst and involving an easy-to-prepare and isolable organoborate reagent.
View Article and Find Full Text PDFPolycyclic polyprenylated acylphloroglucinols from the pericarps of Garcinia multiflora champ. ex Benth. with cytotoxic property.
Phytochemistry
December 2024
State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Avenida da Universidade, Taipa, Macau, 999078, China; Department of Pharmaceutical Sciences, Faculty of Health Sciences, University of Macau, Taipa, Macau, 999078, China. Electronic address:
The phytochemical investigation on the pericarps of Garcinia multiflora resulted in the isolation of 12 previously undescribed polycyclic polyprenylated acylphloroglucinols (PPAPs, 1-12) with a variety of skeletons. Their structures were determined by comprehensive spectroscopic analyses, ECD calculations, and single-crystal X-ray diffraction. Compounds 6-9 possess a rare bicyclo[4.
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