An Efficient One Pot Synthesis of Bicyclic Dienones

Abstract

Bicyclic dienones 4 are prepared in a one pot process from the reaction of 2-(acetoxymethyl)cyclohex-2-enone 1 with 1,3-dicarbonyl compounds 2 in the presence of K 2 CO 3 in refluxing absolute ethanol.

First DMAP-mediated direct conversion of Morita–Baylis–Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates

“…Therefore, an alternative synthesis of γ-aminophosphonates 8 has been developed. Following our previous report [54], we have first converted the MBH alcohol 5 into its acetate 7 in 90% yields using a mixture of Ac 2 O and DMAP as reagents (Scheme 7). …”

Efficient α-chlorination of 2-[(1-oxocyclohex-2-en-2-yl)methyl]-1,3-dicarbonyl Compounds Using Sodium Hypochlorite

“…27 Starting from β-dicarbonyl derivatives 2 in basic conditions, we have also described two synthetic routes to a new series of bicyclic dienones. 28,31 We have also reported the PTSApromoted Robinson annelation of compounds 2, afforded, in a one-pot process, a variety of hydroxytetrahydronaphthyl carbonyl compounds. 32 In connection with our study on the reactivity of the multifunctional derivatives 2, we now report that the use of sodium hypochlorite in the presence of K 2 CO 3 in a commonly available solvent such as THF, is an efficient medium for regioselective monochlorination of a new series of 1,3-dicarbonyl derivatives 2.…”

A Short Route to the Ester (±) HomoSarkomycin via Johnson-Claisen Rearrangement

“…In continuation of our interest in the synthesis of biological compounds [ 21 - 23 ], we established an efficient synthesis of the (±) HomoSarkomycin Ester 2a via a Johnson-Claisen rearrangement using the Baylis-Hillman adduct 1a (Scheme 1 ), that was prepared (in our laboratory) [ 24 ] in one step from 2-cyclopentenone in high yield and in relatively high scale.…”