The conversion of a cycloheptannelated indole platform into the heptacyclic core structure of dragmacidin E proceeded over nine steps. Key sequences include a cyclocondensation to form an intermediate dihydropyrazinone ring and the conversion of a cyclic urea into the cyclic guanidine of the target.
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http://dx.doi.org/10.1021/ol1018008 | DOI Listing |
J Org Chem
January 2025
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutica Sciences, Peking University, Beijing 100191, China.
Arnebidin, a heptacyclic naphthoquinone dimer with a tricyclo[3.3.0.
View Article and Find Full Text PDFChin J Nat Med
March 2024
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. Electronic address:
Hyparillums A (1) and B (2), two previously unidentified polycyclic polyprenylated acylphloroglucinols (PPAPs) with intricate architectures, were isolated from Hypericum patulum Thunb. Hyparillum A was the first PPAP with eight-carbon rings based on an unprecedented 6/6/5/6/6/5/6/4 octocyclic system featuring a rare heptacyclo[10.8.
View Article and Find Full Text PDFJ Am Chem Soc
February 2023
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu, 610041, China.
Vilmoraconitine belongs to one of the most complex skeleton types in the C-diterpenoid alkaloids, which architecturally features an unprecedented heptacyclic core possessing a rigid cyclopropane unit. Here, we report the first total synthesis of vilmoraconitine relying on strategic use of efficient ring-forming reactions. Key steps include an oxidative dearomatization-induced Diels-Alder cycloaddition, a hydrodealkenylative fragmentation/Mannich sequence, and an intramolecular Diels-Alder cycloaddition.
View Article and Find Full Text PDFAdv Mater
January 2023
State Key Laboratory of Powder Metallurgy, Central South University, Changsha, 410083, P. R. China.
The high trap density (generally 10 to 10 cm ) in thin films of organic semiconductors is the primary reason for the inferior charge-carrier mobility and large nonradiative recombination energy loss (ΔE ) in organic solar cells (OSCs), limiting improvement in power conversion efficiencies (PCEs). In this study, the trap density in OSCs is efficiently reduced via extending the donor core of nonfullerene acceptors (NFAs) from a heptacyclic unit to a nonacyclic unit. TTPIC-4F with a nonacyclic unit has stronger intramolecular and intermolecular interactions, affording higher crystallinity in thin films relative to its counterpart BTPIC-4F.
View Article and Find Full Text PDFOrg Lett
March 2022
New Drug Research and Development Center, North China Pharmaceutical Group Corporation, National Microbial Medicine Engineering and Research Center, Hebei Industry Microbial Metabolic Engineering & Technology Research Center, Shijiazhuang 050015, P. R. China.
Five unprecedented chromone derivatives involving a 6/6/5/5/5/6 hexacyclic scaffold (, ), 6/6/5/6/6/6/6 heptacyclic scaffold (), and 6/6/6/5/5/6 hexacyclic scaffold (, ) were obtained from the fungus NCC0415. Their structures were identified using comprehensive spectroscopic analysis, single-crystal X-ray diffraction, and electronic circular dichroism calculations. Except for , the other compounds, especially the 6/6/6/5/5/6 hexacyclic derivatives ( and ), exhibited potent inosine-5'-monophosphate dehydrogenase (IMPDH) inhibitory activities.
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