In this issue, Suh's group reported a new formal total synthesis of (±)-grandisol featuring a palladium-catalyzed 4-exo-trig cyclization. Grandisol's interesting cyclobutane structure has been a popular test model for various cyclization methods over the years. This report summarizes Suh's formal synthesis of grandisol along with a concise review of the four-membered ring cyclization strategies employed in the synthesis of grandisol.
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Catalytic enantioselective synthesis of benzocyclobutenols and cyclobutanols a sequential reduction/C-H functionalization.
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August 2021
Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University 220 Handan Lu Shanghai 200433 P. R. China
We report here a sequential enantioselective reduction/C-H functionalization to install contiguous stereogenic carbon centers of benzocyclobutenols and cyclobutanols. This strategy features a practical enantioselective reduction of a ketone and a diastereospecific iridium-catalyzed C-H silylation. Further transformations have been explored, including controllable regioselective ring-opening reactions.
View Article and Find Full Text PDFRing-Expansion Induced 1,2-Metalate Rearrangements: Highly Diastereoselective Synthesis of Cyclobutyl Boronic Esters.
J Am Chem Soc
March 2020
School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, U.K.
The broad synthetic utility of organoboron compounds stems from their ready ability to undergo 1,2-migrations. Normally, such shifts are induced by α-leaving groups or by reactions of alkenyl boronates with electrophiles. Herein, we present a new strategy to induce 1,2-metalate rearrangements, via ring expansion of vinylcyclopropyl boronate complexes activated by electrophiles.
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J Chem Ecol
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Eco-Chemistry, Department of Chemical Engineering, Mid Sweden University, SE-851 70, Sundsvall, Sweden.
The bark beetle Polygraphus punctifrons (Coleoptera: Curculionidae) is a species that feeds on Norway spruce (Picea abies) and is found in the Northern parts of Europe and Russia. The release of volatile organic compounds (VOCs) produced by males and females of P. punctifrons when the beetles bore into spruce stem sections in a laboratory environment was studied using solid phase microextraction (SPME).
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J Am Chem Soc
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Department Chemie and Catalysis Research Center (CRC) , Technische Universität München, Lichtenbergstrasse 4 , 85747 Garching , Germany.
The intermolecular [2+2] photocycloaddition of typical cyclic α,β-unsaturated enones, such as 2-cyclohexenone, with olefins was performed in moderate to good yields (42-82%) and with high enantioselectivity (82%-96% ee). An unusual substitution pattern at the chiral oxazaborolidine-AlBr Lewis acid complex that promotes the reaction was found to be crucial for the success of the reaction. The method was applied to the enantioselective synthesis of the monoterpene (-)-grandisol, which could be accomplished in six steps and with an overall yield of 13% starting from 3-methyl-2-cyclohexenone.
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Department of Pathology, The First Hospital of Wuhan, Wuhan, Hubei 430033, P.R. China.
The aim of the present study was to investigate the chemical composition of the essential oil of Artemisia vestita and to determine the antibacterial activity of the essential oil and its two major components, grandisol and 1,8‑cineole, against certain respiratory infection‑causing bacterial strains, in vitro and in vivo. The chemical composition of the essential oil was analyzed using gas chromatography‑mass spectrometry. A micro‑well dilution method was used to determine the minimum inhibition concentration (MIC) values of the essential oil and its major constituents.
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