Abstract:Two enantiomeric pairs of meroterpenoids, (-)- and (+)-rhodonoids A (1a and 1b) and B (2a and 2b), were isolated unprecedentedly from partially racemic mixtures that naturally occurred in Rhododendron capitatum. Their structures were fully determined by spectroscopic data, X-ray crystallography, and electronic circular dichroism analysis. Compounds 1a and 1b are the first examples of meromonoterpenes featuring a unique 6/6/6/4 ring system. Compounds 2a and 2b showed PTP1B inhibitory activity.
“…It is also notable that all the compounds with exception of 18 and 25 were isolated as racemates, actually numerous racemic natural products have been also isolated from plants. 16,17 Although natural compounds are normally considered as enzyme-catalyzed products, the fact that racemic products were isolated might be closely associated with their minor nature in the organisms. …”
Section: H Cosy Spectrum Of 20 (Supplementary Material) Shows That Comentioning
“…It is also notable that all the compounds with exception of 18 and 25 were isolated as racemates, actually numerous racemic natural products have been also isolated from plants. 16,17 Although natural compounds are normally considered as enzyme-catalyzed products, the fact that racemic products were isolated might be closely associated with their minor nature in the organisms. …”
Section: H Cosy Spectrum Of 20 (Supplementary Material) Shows That Comentioning
“…Many of the natural products arise directly from photochemical [2 + 2] dimerization processes of simpler alkene building blocks, as in the truxillic and truxinic acids (from cinnamic acid) 16 and sceptrin (from hymenidin). 17 Beyond these dimeric compounds, arylcyclobutane scaffolds are also observed in monoterpenoids such as cannabicyclol, 18 murrayamine M, 19 rhodonoids A and B, 20 and cochlearol B. 21 Arylcyclobutanes are considered intriguing systems for drug discovery because they place functionality in a defined spatial orientation.…”
Recent developments in controlled C-H functionalization transformations continue to inspire new retrosynthetic disconnections. One tactic in C-H functionalization is the intermolecular C-H insertion reaction of rhodium-bound carbenes. These intermediates can undergo highly selective transformations through the modulation of the ligand framework of the rhodium catalyst. This work describes our continued efforts toward differentiating C-H bonds in the same molecule by judicious catalyst choice. Substituted cyclobutanes that exist as a mixture of interconverting conformers and possess neighboring C-H bonds within a highly strained framework are the targets herein for challenging the current suite of catalysts. Although most C-H functionalization tactics focus on generating 1,2-disubstituted cyclobutanes via substratecontrolled directing-group methods, the regiodivergent methods discussed in this paper provide access to chiral 1,1-disubstituted and cis-1,3-disubstituted cyclobutanes simply by changing the catalyst identity, thus permitting entry to novel chemical space.
“…The polycyclic compounds are widely found in natural products [3], drug molecules [4] and bioactive compounds, [5] and due to the complicated structure and potential biological activity, the development of new methods for the synthesis of novel polycyclic compounds is of great insterest. As part of our continuing efforts on the efficient synthetic methods for cyclic compounds synthesis, [6] herein, we report a useful method and the crystal structure of the titled compound.…”
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.