Synthesis of an epoxyquinol analog: efficient methodology for the insertion of side chains into cyclohexenone cores

Synthesis of Functionalized Ring C of Escobarines

“…Introduction of the required hydroxymethyl group on the β‐carbon of cyclohexenone could also be accomplished by the umpolung effect10 where the C‐3 becomes nucleophilic in the presence of an arylsulfone, after protection of the ketone (Scheme ) 11. Michael addition of sodium p ‐toluenesulfinate and protection of the ketone gave the sulfone 13 .…”

“…Completion of the synthesis of the functionalized ring C of escobarines C is shown in Scheme . Palladium cross‐coupling of α‐iodoenone 19 with ethynyltrimethylsilane gave the enynone 21 in good yield 11. A longer reaction time and higher temperatures were crucial to obtain high yields in the Sonagashira coupling.…”

Retrosynthetic strategies and their impact on synthesis of arcutane natural products

“…Still, elements from the earlier synthesis of atropurpuran by Qin are also evident in Xu's strategy. For example, Xu's introduction of C18 and reduction of the penultimate intermediate (36), both proceeded analogously to transformations in the Qin synthesis. In addition, both groups utilized an oxidative dearomatization/intramolecular Diels-Alder sequence, a powerful, well-established way to generate [2.2.2]bicycles in diterpenoid alkaloid synthesis.…”

Crystal structure and absolute configuration of (3aR,3′aR,7aS,7′aS)-2,2,2′,2′-tetramethyl-3a,6,7,7a,3′a,6′,7′,7′a-octahydro-4,4′-bi[1,3-benzodioxolyl], obtained from a Pd-catalyzed homocoupling reaction

“…Over the last few years, we have focused our efforts on the synthesis of vinylsulfimines as precursors in -lactamization reactions to generate asymmetric pyrrolidone derivatives which are of interest in medicinal chemistry (Silveira et al, 2012(Silveira et al, , 2014Silveira & Marino, 2013;Pereira et al, 2015). Encouraged by our previous experience in functionalizing halo-cyclohexadiendiols (Heguaburu et al, 2008;Labora et al, 2010;Heguaburu et al, 2010;Labora et al, 2008), we synthesized a vinylic sulfide (molecule 3 in Fig. 1) from protected iodo-cyclohexenediol (molecule 1 in Fig.…”