UnprecedentedE-stereoselectivity on the sigmatropic Hurd–Claisen rearrangement of Morita–Baylis–Hillman adducts: a joint experimental–theoretical study

Abstract

Non-covalent interactions as the origin of the stereoselectivity.

α-Alkylidene δ-lactones inhibit quorum sensing phenotypes inChromobacteriumstrain CV026 showing interaction with the CviR receptor

“…The aldehydes 8 were obtained in a stereoselective way by a previously reported route of synthesis, starting from Morita–Baylis–Hillman adducts prepared with readily available aldehydes 4 and ethyl acrylate 5. 33 …”

“…The α-alkylidene δ-lactones of this study were synthesized as described by Machado and co-workers. 33 …”

Synthesis of novel sulfide-based cyclic peptidomimetic analogues to solonamides

“…Two MBH adducts ( 2 ) (R = Me, heptyl) and their respective carboxylic acids 3 were obtained in good yields based on previously reported procedures (Scheme 2) [35–36].…”

Stereoselective Synthesis of (±)-Cephanolide B

“…The Morita–Baylis–Hillman reaction of methyl acrylate 12 with acetaldehyde proceeded in the presence of DABCO in a dioxane/H 2 O mixed solvent (1:1, v/v) at 0 to 25 °C for 24 h to give allylic alcohol 14 in 82%. To prepare the dienophile 12 , allylic alcohol 14 was reacted with vinyl ether 15 using Hg­(OAc) 2 as catalyst in Et 3 N at 90 °C to afford intermediate 13 , which then underwent a thermal [3,3]-sigmatropic rearrangement to afford dienophile 12 as a pair of regioisomers in a 4:1 ratio. without separation, compound 12 was then reacted with Danishefsky’s diene 11 in mesitylene at 200 °C in a sealed tube.…”