A concise synthesis of paraconic acids: (−)-methylenolactocin and (−)-phaseolinic acid

Fernandes, Rodney A.; Chowdhury, Asim K.

doi:10.1016/j.tetasy.2011.05.007

Cited by 21 publications

(6 citation statements)

References 87 publications

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“…In addition, (À)-phaseolinic acid (9), isolated from culture filtrates of fungi such as Macrophomina phaseolina, was synthesized from 3 s via the chiral g-lactone intermediate (8). [25] In summary, we developed a CuH-catalyzed asymmetric reductive conjugate addition of borylalkenes to a,b-unsaturated diesters with high chemo-, diastereo-, and enantioselectivity. This method provides efficient and direct access to enantioenriched alkylboron compounds carrying two contig-uous stereogenic centers by assembling readily available starting alkenyl reagents in a single operation without using preformed organometallic reagents or chiral auxiliaries, which greatly expands the scope of asymmetric conjugate addition.…”

Section: Angewandte Chemiementioning

confidence: 99%

Asymmetric Conjugate Addition of Chiral Secondary Borylalkyl Copper Species

2021

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We report the diastereo‐ and enantioselective conjugate addition of chiral secondary borylalkyl copper species derived from borylalkenes in situ to α,β‐unsaturated diesters. In the presence of a chiral bisphosphine‐ligated CuH catalyst, the conjugate addition provides a direct access to enantioenriched alkylboron compounds containing two contiguous carbon stereogenic centers in good yield with high diastereo‐ and enantioselectivity (up to >98:2 dr, >99:1 er) by assembling readily available starting alkenyl reagents in a single operation without using preformed organometallic reagents or chiral auxiliaries. The resulting products were used in various organic transformations. The utility of the synthetic approach was highlighted by the synthesis of (−)‐phaseolinic acid.

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Section: Angewandte Chemiementioning

confidence: 99%

Asymmetric Conjugate Addition of Chiral Secondary Borylalkyl Copper Species

2021

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“…In 2011, we considered regioselective asymmetric dihydroxylation and orthoester Johnson–Claisen rearrangement as key steps in the synthesis of (−)‐methylenolactocin and (−)‐phaseolinic acid (Scheme ) . Addition of lithiated ethyl propiolate 84 to hexanal afforded the hydroxy alkynoate 85 .…”

Section: Synthesis Of Paraconic Acidsmentioning

confidence: 99%

Evolution of Strategies in Paraconic Acids Synthesis

2020

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Various syntheses of different paraconic acids over the last seventeen years have been abstracted here. Paraconic acids have either a methylene or methyl group at the 4-position of the γ-butyrolactone with a common C-3 carboxylic acid group and a long alkyl chain. Several possibilities of relative configurations give rise to distinct set of paraconic acids, which are also categorized in this review. Various strategies based on chiral catalytic methods, chiral pool, chiral auxiliary, resolution and other methods were engaged in the synthesis of different paraconic acids. A few members are yet to be synthesized and this compilation might entice future synthetic attempts on them.

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“…In a stereodivergent approach using both diastereomeric lactones obtained from Johnson-Claisen rearrangement of an acetonide-containing allyl alcohol, Fernandes [155] later disclosed the total syntheses of (-)-methylenolactocin (275, Scheme 52) [152] and (-)-phaseolinic acid (276). [156] The hydroxy alkynoate 271, obtained from hexanal, was transformed into allyl alcohol 272.…”

Section: Scheme 44 Syntheses Of Primin and Primin Acidmentioning

confidence: 99%

The Orthoester Johnson–Claisen Rearrangement in the Synthesis of Bioactive Molecules, Natural Products, and Synthetic Intermediates – Recent Advances

2013

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The orthoester Johnson–Claisen rearrangement, an important C–C bond forming reaction, has been used enormously in the past four decades in the synthesis of bioactive molecules, natural products, synthetic intermediates, analogues, and useful building blocks. The method has also featured in chemical modification of materials. This review covers developments in this rearrangement since 2003. Unlike many other forms of Claisen rearrangement, this reaction is generally a one‐pot, one‐step process. It is compatible with numerous functional groups, despite its use of acid catalysis, and offers chirality transfer to produce stereoselective products. The method also offers opportunities for rapid modifications to various functionalized compounds and building blocks for further synthetic exploration.

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A concise synthesis of paraconic acids: (−)-methylenolactocin and (−)-phaseolinic acid

Cited by 21 publications

References 87 publications

Asymmetric Conjugate Addition of Chiral Secondary Borylalkyl Copper Species

Asymmetric Conjugate Addition of Chiral Secondary Borylalkyl Copper Species

Evolution of Strategies in Paraconic Acids Synthesis

The Orthoester Johnson–Claisen Rearrangement in the Synthesis of Bioactive Molecules, Natural Products, and Synthetic Intermediates – Recent Advances

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