Asymmetric synthesis of a model compound for the cyclohexenone core of ambuic acid

Labora, Maitia; Heguaburu, Viviana; Pandolfi, Enrique; Schapiro, Valeria

doi:10.1016/j.tetasy.2008.03.023

Cited by 13 publications

(7 citation statements)

References 19 publications

(15 reference statements)

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“…1) which is used as a precursor in enantioselective syntheses of epoxycyclohexenone compounds. Model compounds of the central core of ambuic acid (Labora et al, 2008), (+)-and (À)bromoxone (Labora et al, 2010), an epoxyquinol analog (Heguaburu et al, 2010), gabosine A, ent-epoformin and entepiepoformin (Labora et al, 2011) have been prepared starting from the same precursor. The title compound, diol (3) (see Fig.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and absolute configuration of (3aS,4S,5R,7aR)-2,2,7-trimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxole-4,5-diol

et al. 2015

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Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and absolute configuration of (3aS,4S,5R,7aR)-2,2,7-trimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxole-4,5-diol

et al. 2015

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“…(+)-Epoxyquinol A (28) was isolated from an uncharacterized fungus from a soil sample, exhibiting potent angiogenesis inhibition properties [15]. (+)-Epoxyquinol A (28) was isolated from an uncharacterized fungus from a soil sample, exhibiting potent angiogenesis inhibition properties [15].…”

Section: Sources and Biological Activitiesmentioning

confidence: 99%

“…They have been widely used for the synthesis of a great variety of natural polyoxygenated products [78][79][80][81]. In 2008, we have reported the synthesis of a model compound of the central core of ambuic acid [28], starting from toluene as the aromatic substrate to be biotransformed into the corresponding cisdiol by Pseudomonas putida F39/D [76]. In 2008, we have reported the synthesis of a model compound of the central core of ambuic acid [28], starting from toluene as the aromatic substrate to be biotransformed into the corresponding cisdiol by Pseudomonas putida F39/D [76].…”

Section: Use Of Microbial Chiral Building Blocksmentioning

confidence: 99%

Enantioselective Synthesis of Natural Epoxyquinoids

Pandolfi

Schapiro²,

Heguaburu³

et al. 2013

COS

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Natural products play an important role as a source not only of potential therapeutic drugs but also of starting materials for semisynthetic new medicines. The epoxyquinoid family, composed by cyclohexane epoxides and related structures, exhibit these characteristics without doubt.Since 2004, significant efforts have been devoted to the stereocontrolled synthesis of these molecules with different and interesting strategies. More than 50 works on this field have been published during this period of time. In addition, many of these polyoxygenated cyclohexenoids exhibit diverse and impressive bioactive shapes. This review aims to analyze the recent advances in the enantioselective processes that have been performed for the total syntheses of these target molecules. It includes a wide range of methodologies for the introduction of chirality either enzymatic or chemical ones. This summarizes microbial preparation of starting materials, lipase kinetic resolutions, use of compounds from the chiral pool, use of chiral auxiliaries and asymmetric catalysis. In a special section, syntheses of scyphostatin are also included.

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“…A inserção de uma cadeia alílica em derivados de cis-dióis, combinada com modernas metodologias sintéticas, tem sido empregada como estratégia 67 para a síntese total de epoxienonas quirais, como o ácido ambuico, a jesterona e os epoxiquinóis. 68 Com este objetivo, foi desenvolvido um novo método para a formação dos alilcicloalcenos 34, a partir do acoplamento cruzado de Stille 69 entre os haletos vinílicos 31 e 32 e aliltributilestanana (33), na presença de um catalisador de paládio (Esquema 12). 70 Foram realizados estudos comparativos variandose a fonte de aquecimento (banho de óleo ou microondas), constatando-se que, de modo geral, os tempos de reação foram sensivelmente reduzidos quando a reação foi conduzida no MW-MESO.…”

Section: Acoplamento De Stille Catalisado Por Paládiounclassified

The Microwave Reactor at MESO-Lab/UFSC: Four Years Accelerating Reactions, Breakthroughs and Opportunities

Sá¹,

Meier²,

Dutra³

et al. 2010

Revista Virtual De Química

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Reactions performed under microwave irradiation offer many advantages when compared to conventional ones, including short reaction times, high yields, controlled selectivity, and low energy consumption, as well as the possibility to perform solvent-free transformations with lower production of residues under safer and more environmentally benign conditions. In this mini-review, we describe several examples of reactions performed since 2006 in a monomode microwave reactor, located at MESO-Lab (Laboratory of Organic Synthesis and Methodology, Chemistry Department, UFSC), by our research group as well as by others from Brazil and Uruguay. The reactions described herein are organized into topics according to whether the main step involves the formation (or cleavage) of C-N, CO or CC bonds.

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Asymmetric synthesis of a model compound for the cyclohexenone core of ambuic acid

Cited by 13 publications

References 19 publications

Crystal structure and absolute configuration of (3aS,4S,5R,7aR)-2,2,7-trimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxole-4,5-diol

Crystal structure and absolute configuration of (3aS,4S,5R,7aR)-2,2,7-trimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxole-4,5-diol

Enantioselective Synthesis of Natural Epoxyquinoids

The Microwave Reactor at MESO-Lab/UFSC: Four Years Accelerating Reactions, Breakthroughs and Opportunities

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