The label from [3-(13)C]-L-glycerol is incorporated into the hydroxymethyl group of methylenomycin furans suggesting a butenolide intermediate in their biosynthesis.
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http://dx.doi.org/10.1039/c000496k | DOI Listing |
Chem Asian J
December 2024
Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008, India.
We present a comprehensive account of our efforts directed towards the synthesis of sacubitril, a neprilysin inhibitor used in combination with valsartan and marketed as Entresto™. Our initial approach to the formal synthesis of sacubitril employed a chiral pool strategy, utilizing (S)-pyroglutamic acid as a key building block and Cu(I)-mediated Csp-Csp cross-coupling as a key transformation. Further investigations led to the development of chiral amine transfer (CAT) reagents-based stereoselective synthesis.
View Article and Find Full Text PDFACS Omega
November 2024
School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland 1010, New Zealand.
The synthesis of the spirocyclic imine fragment of the portimine family of marine toxins has been achieved. A densely functionalized key lactone-ester intermediate was assembled via a highly diastereoselective Diels-Alder cycloaddition, involving a novel γ-hydroxymethyl-α,β-butenolide dienophile. A Stille coupling was employed to install the vinyl group.
View Article and Find Full Text PDFiScience
September 2024
University of Alcala, Department of Biomedicine and Biotechnology, 28805 Alcalá de Henares, Spain.
Fast and efficient galvanostatic conversion of 2,4-diarylfurans into dimeric furan-2(5)-ones is now possible in one pot and good yields at room temperature in sustainable aqueous organic solvent. Recent applications of these highly desired structures demand our attention since they are a versatile alternative to acrylates in polymerization to achieve green materials. The reaction mechanism proposal, supported by density functional theory (DFT) theoretical calculations, involves furanoxy radicals, detected by electron paramagnetic resonance (EPR), as the last intermediate before a homocoupling step that affords butenolides.
View Article and Find Full Text PDFOrg Lett
October 2023
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States.
The synthesis of heretofore unknown γ-spirobutenolides has been achieved via an -CPBA-mediated oxidation of β-furyl amides. The reaction employs a tethered amide, ostensibly a poorly reactive carbonyl, as a nontraditional nucleophile resulting in spirolactone formation and concurrent amide cleavage. The transformation exhibits functional group tolerance and compatibility with complex compounds.
View Article and Find Full Text PDFOrg Biomol Chem
May 2023
Institute of Nanoscience & Nanotechnology, NCSR "Demokritos", Ag. Paraskevi, Athens, Greece.
The intramolecular Diels-Alder reaction (IMDA) of a butenolide derivative, as an entry to the type II abyssomicin scaffold, and the total synthesis of (±)-abyssomicin 2 and (±)-neoabyssomicin B are reported for the first time. A facile route to the IMDA precursor, the formation of a type I intermediate and two paths to (±)-neoabyssomicin B are also discussed.
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