Studies on synthesis and photoreaction of tricycloundecanes endowed with β,γ-enone chromophore: Towards angular triquinanes and annulated bicyclo[4.2.0]octanes

An Efficient Synthesis Towards the Core of Crinipellin and Alliacol-B Along With Their Docking Studies

“…The behaviour of tetracyclic compound 4is same with previous tricyclic chromophoric systems 14 under photochemical transformation 8. As, the 1,3-acyl shift product 15 was formed as a major amount in both direct irradiation as well as sensitized irradiationof compound 14, It was converted to its tricyclic lactone 16which is a core ofAlliacol B.…”

“…6 approach for creating molecular complexity by engaging oxidative dearomatization of ohydroxymethyl phenols, cycloaddition, and photochemical reactions. 7 Taking into consideration of interest towards crinipellin1, as well as alliacol B2, we extended our previous approach towards angular triquinane 8 to tetraquinane and alliacol B. Herein, we wish to report a novel route for the synthesis of the tetracyclic ring systems 1e, which is a common core of crinipellin via oxidative dearomatization, cycloaddition and oxa-di-pimethane rearrangement.…”

“…The aromatic precursors 6 would be readily prepared from 5-methoxy indanone. 8 As we all know that the ongoing COVID-19 outbreak driven by highly infectious SARS-CoV-2 and causing the current pandemic and has turned on the most critical universal health disaster of this century [9,10]. So, after synthesizing the compounds, we have performed the molecular docking studies against some selected proteins/enzymes receptors by using CLC Drug Discovery Workbench Software.…”

Total Synthesis of (+)-Viridianol, a Marine-Derived Sesquiterpene Embodying the Decahydrocyclobuta[d]indene Framework

“…This work also emphasizes the utility of the Givens-type rearrangement of bicyclo[2.2.2]octenones as a means for generating cyclobutannulated cyclohexenes in a range of settings, including ones where the photoproduct incorporates an all-carbon quaternary center. 20 ■ EXPERIMENTAL SECTION General Experimental Procedures. Unless otherwise specified, proton ( 1 H) and carbon ( 13 C) NMR spectra were recorded at room temperature in base-filtered CDCl 3 on a Varian spectrometer operating at 400 MHz for proton and 100 MHz for carbon nuclei.…”

“…Concentration of the relevant fractions (R f = 0.7) then gave compound 12 (10.0 g, 60%) as a clear, colorless liquid. 1 H NMR (400 MHz, CDCl 3 ) δ 5.60 (m, 1H), 5.02 (m, 2H), 3.30− 3.10 (complex m, 2H), 2.28 (m, 1H), 1.80 (m, 2H), 1.02 (d, J = 6.7 Hz, 3H); 13 C NMR (101 MHz, CDCl 3 ) δ 142.5, 114.1, 40.0, 38.7, 19.7, 4.9; IR (KBr) ν max 3077, 2958, 2920, 1640, 1452, 1418, 1373, 1238, 1179, 994, 917 cm −1 ; MS (EI, 70 ev) m/z 210 (M +• , 21%), 209 (95), 155 (15), 127 (20), 83 (40) 81 (38), 55 (100). Satisfactory high-resolution mass spectral data could not be obtained for this compound.…”