The total synthesis of enhygrolide A, a γ-alkylidene butenolide natural product which exhibits antibacterial activities, is reported. The synthetic route features several key transformations, including a copper mediated Sonogashira/oxacyclization 5-exo-dig process to generate the alkylidene butenolide system and a Suzuki cross-coupling to introduce the benzylic unit. The methodology employed for this total synthesis represents a sufficiently flexible route to allow the synthesis of numerous analogs of these enhygrolides.
Carboxylate-directed tandem functionalisations of α,β- dihaloalkenoic acids with 1-alkynes: A straightforward access to (Z)-configured, α,β-substituted γ-alkylidenebutenolides
An easy and mild copper(I)-catalysed lactonisation of readily available (E)-2,3-dihalopropenoic acid derivatives regio- and stereoselectively leads to rarely described (Z)-3-halo-5-ylidene-5H-furan-2-ones. These compounds are subsequently able to undergo classical Pd-catalysed cross-coupling reactions, providing 3-substituted and 3,4-disubstituted 5-ylidene-5H-furan-2-ones (see scheme).
Stereoselective synthesis of (E)-2,3-Dibromobut-2-enoic acid: (2-Butenoic acid, 2,3-dibromo-, (2E)-)
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Ngi, Samuel Inack,Anselmi, Elsa,Abarbri, Mohamed,Langle, Sandrine,Duchêne, Alain,Thibonnet, Jér?me,Bhat, Vikram,Rawal, Viresh H.
p. 231 - 237
(2017/09/08)
Selective synthesis of dihalo-substituted unsaturated carboxylic acids and derivatives
A selective one-pot procedure was developed for the production of E-dihalo-substituted α,β-unsaturated alkenoic acids and derivatives from the corresponding α,β-unsaturated alkynoic acids. Georg Thieme Verlag Stuttgart.
Langle, Sandrine,Ngi, Samuel Inack,Anselmi, Elsa,Abarbri, Mohamed,Thibonnet, Jerome,Duchene, Alain
p. 1724 - 1728
(2008/02/05)
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