Novel Synthons from Mucochloric Acid:  The First Use of α,β-Dichloro-γ-butenolides and γ-Butyrolactams for Direct Vinylogous Aldol Addition

Sarma, Koushik Das; Zhang, Ji; Curran, Timothy T.

doi:10.1021/jo062613l

Cited by 52 publications

(39 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…13 We anticipated that as furyl unit is more polar than the phenyl ring, the introduction of this heteroaromatic moiety could result in more active substances. The appendage of the C5 substituents at compounds 6 and 9 can be achieved in two steps by aldol condensation followed by elimination of water 20 or by a one-pot arylmethylenation procedure developed by Boukouvalas 17,21 and several procedures were reported for the aldol reaction involving butenolide 4. Initially, we tried the new condensation protocol described by Xu et al, 22 but contrary to what they reported, only one product was isolated from the hydrolysis of the butenolide.…”

Section: Synthesismentioning

confidence: 99%

Tailoring nostoclide structure to target the chloroplastic electron transport chain

Barbosa¹,

Varejão²,

Petrollino³

et al. 2011

Arkivoc

View full text Add to dashboard Cite

Aiming to improve their effectiveness, three modifications were introduced into the structure of the natural phytotoxins nostoclides, leading to the synthesis of novel 3-benzyl-4-isopropyl-5-(arylmethylene)furan-2(5H)-ones, 3-benzyl-5-(furan-2-ylmethylene)furan-2(5H)-ones, and 3,4-dihalo-5-arylidenefuran-2(5H)-ones. All compounds were characterized by IR, 1 H and 13 C NMR, NOEDIF, COSY, HETCOR and MS spectrometry. Increasing the length of the molecule was found to reduce the ability to interfere with ferricyanide reduction by isolated chloroplasts. The addition of an isopropyl moiety into the heterocyclic ring, as in naturally-occurring nostoclides, did not influence the inhibitory potential. Also the replacement of the electron-drawing phenyl substituent with two halogen residues did not improve the resulting activity. However, both latter modifications influenced the interaction with the photosynthetic machinery. These analogues could therefore represent novel leads to be explored toward the development of new herbicides targeting the chloroplastic electron transport chain.

show abstract

Section: Synthesismentioning

confidence: 99%

Tailoring nostoclide structure to target the chloroplastic electron transport chain

Barbosa¹,

Varejão²,

Petrollino³

et al. 2011

Arkivoc

View full text Add to dashboard Cite

show abstract

“…36 As reações foram realizadas em metanol na presença de 0,5 equivalentes de trietilamina (Tabela 5).…”

Section: Reações Da 34-dibromofuran-2(5h)-ona -Adição Nucleofílica àunclassified

“…36 Neste cenário, Terada e colaboradores desenvolveram a reação homo-aldol assimétrica catalisada por guanidinas cíclicas quirais 56a-h (Figura 5). 38 A criação de dois centros adjacentes de configuração definida em uma única etapa, com 100% de economia atômica, coloca esta reação em destaque na química de 2.…”

Section: Figura 5 Guanidinas Cíclicas Quirais Organocatalisadores Emunclassified

Aplicações sintéticas do ácido mucobrômico e da 3,4-dibromofuran-2(5H)-ona

Cunha¹,

Oliveira²

2011

Quím. Nova

View full text Add to dashboard Cite

Recebido em 23/11/10; aceito em 1/4/11; publicado na web em 10/6/11 SYNTHETIC APPLICATIONS OF MUCOBROMIC ACID AND 3,4-DIBROMOFURAN-2(5H)-ONE. This review describes the use of two biomass-derivate butenolides as intermediates in organic synthesis, mucobromic acid and its reduced derivative 3,4-dibromofuran-2(5H)-one. The ambiphilic and ambident character of such butenolides make them versatile starting materials in the synthesis of natural and/or bioactive compounds. Thus, the reactions of mucobromic acid with C-nucleophiles and heteronucleophiles are described, as well as the nucleophilic addition to carbonyl reactions of 3,4-dibromofuran-2(5H)-one. Besides, both compounds are active in diverse metal cross-coupling reactions, manly with palladium in Suzuki and Sonogashira reactions.Keywords: mucobromic acid; 3,4-dibromofuran-2(5H)-one; butenolides. INTRODUÇÃOA ciência Síntese Orgânica passa por um momento de revitalização que inclui, entre outros aspectos, a preocupação com a eficiência da metodologia sintética e sua aplicação numa síntese total, quer seja um produto natural ou uma substância valorada por suas propriedades biológicas ou físico-químicas.1-3 A incorporação de materiais de partida obtidos de fontes renováveis, a preocupação com o menor consumo de energia, o emprego de métodos e técnicas para acelerar e/ou promover reações antigas e novas passaram a ser metas do planejamento sintético.4,5 Estas modificações podem ser relacionadas com incrementos no design experimental. Desta forma, Carlson propôs o conceito da reação ideal, que deve ser realizada em água, o material de partida de fácil acesso, barato, não tóxico e o produto facilmente isolado em rendimento quantitativo. 6 Complementarmente, Wender preconizou que a economia de etapas é o fator de maior influência na viabilidade de uma síntese, pois determina tempo, custo, geração de resíduos e escala do processo.7 Portanto, novas reações devem ser desenvolvidas para que os princípios da Química Verde sejam atendidos.8 Estas condições de idealidade para uma síntese norteiam os desafios a serem perseguidos pela comunidade sintética no século atual.Uma das formas de se obter, em poucas etapas, um aumento significativo de complexidade estrutural consiste em empregar molé-culas polifuncionalizadas ambifílicas e polidentadas de fácil acesso, que possam, assim, atuar como eletrófilos e/ou nucleófilos. Dentre as que apresentam todas estas características, merecem destaque as furanonas halogenadas como o ácido mucobrômico (1) e o seu derivado reduzido, a 3,4-dibromofuran-2(5H)-ona (2) (Figura 1).

show abstract

“…Zhang and co-workers first utilized a,b-dichloro-gbutenolides in the direct vinylogous aldol reaction. [11] Recently, Terada and co-workers reported an enantioselective vinylogous aldol reaction of furanone derivatives with aldehydes catalyzed by a chiral guanidine. [12] Feng and coworkers subsequently disclosed a thiourea-catalyzed direct vinylogous aldol reaction of furanones with aldehydes.…”

mentioning

confidence: 99%

The Direct Asymmetric Vinylogous Aldol Reaction of Furanones with α‐Ketoesters: Access to Chiral γ‐Butenolides and Glycerol Derivatives

et al. 2011

View full text Add to dashboard Cite

Novel Synthons from Mucochloric Acid: The First Use of α,β-Dichloro-γ-butenolides and γ-Butyrolactams for Direct Vinylogous Aldol Addition

Cited by 52 publications

References 35 publications

Tailoring nostoclide structure to target the chloroplastic electron transport chain

Tailoring nostoclide structure to target the chloroplastic electron transport chain

Aplicações sintéticas do ácido mucobrômico e da 3,4-dibromofuran-2(5H)-ona

The Direct Asymmetric Vinylogous Aldol Reaction of Furanones with α‐Ketoesters: Access to Chiral γ‐Butenolides and Glycerol Derivatives

Contact Info

Product

Resources

About