The stereochemistry of 2,4- and 2,3-disubstituted-γ-butyrolactones

Hussain, S. A. M. Tayyeb; Ollis, W. D.; Smith, Christopher; Stoddart, J. Fraser

doi:10.1039/p19750001480

Cited by 55 publications

(28 citation statements)

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“…Methacryloyl chloride ( 12 ) was esterified with but-3-en-2-ol ( 13 ) in the presence of triethylamine to yield but-3-en-2-yl methacrylate ( 15 ). Ring-closing metathesis with Grubbs catalyst of the second generation gave 2-methylpent-2-en-4-olide ( 11 ) that upon catalytic hydrogenation yielded cis -2-methylpentan-4-olide ( 7 ) as a single diastereomer, as reported previously [ 28 ]. Under prolonged treatment with KO t -Bu in t -BuOH under reflux, partial isomerisation to trans -2-methylpentan-4-olide ( 8 ) was achieved.…”

Section: Resultssupporting

confidence: 76%

Algicidal lactones from the marine Roseobacter clade bacterium Ruegeria pomeroyi

Riclea¹,

Gleitzmann²,

Bruns³

et al. 2012

Beilstein J. Org. Chem.

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SummaryVolatiles released by the marine Roseobacter clade bacterium Rugeria pomeroyi were collected by use of a closed-loop stripping headspace apparatus (CLSA) and analysed by GC–MS. Several lactones were found for which structural proposals were derived from their mass spectra and unambiguously verified by the synthesis of reference compounds. An enantioselective synthesis of two exemplary lactones was performed to establish the enantiomeric compositions of the natural products by enantioselective GC–MS analyses. The lactones were subjected to biotests to investigate their activity against several bacteria, fungi, and algae. A specific algicidal activity was observed that may be important in the interaction between the bacteria and their algal hosts in fading algal blooms.

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Section: Resultssupporting

confidence: 76%

Algicidal lactones from the marine Roseobacter clade bacterium Ruegeria pomeroyi

Riclea¹,

Gleitzmann²,

Bruns³

et al. 2012

Beilstein J. Org. Chem.

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“…The 7-butyrolactone substituents are in positions 2 and 4 and are cis to each other according to the generally accepted opinion that the cis isomers are more stable than the corresponding trans isomers. The present structure analysis also confirms that the difference in free energies between the cis and trans isomers of the 7-butyrolactone envelope conformers is rather small as suggested by Hussain, Ollis, Smith & Stoddart (1975). All bond lengths and angles are within the expected values and agree well with those found in other y-butyrolactone structures (Sikirica, Vickovi6 & Viterbo, 1979).…”

supporting

confidence: 88%

4-Methylthio-2-phthalimido-γ-butyrolactone

Bruvo¹,

Sikirica²,

Vicković³

1981

Acta Crystallogr Sect B

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with the phases from the set with the highest combined figure of merit revealed peaks for the complete molecule except for one C atom from the six-membered ring. All non-hydrogen atoms were then refined isotropicaUy and anisotropically by means of the full-matrix leastsquares method using the XRAY 72 system of programs (Stewart, Kruger, Ammon, Dickinson & Hall, 1972). The function minimized was ~ w(IFolIFcl)2/~ WlFo 12 where w was defined as w = 1/cr2(Fo).

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“…[14] This unsaturated lactone 5 was reduced under hydrogenation over 10 % Pd/C in EtOAc to set up the hydroxyl function and methyl substituents in cis relative configuration via a 1,3induced asymmetric hydrogenation. [15] The disclosed secondary alcohol of 6 was protected as its TBS ether in 93 % yield and the protected lactone 7 was reduced with DIBAL-H to yield the lactol 8 and acetylated to provide the more stable O-acyl lactol 9 in good yields.…”

mentioning

confidence: 99%

Total Synthesis of the Fungal Metabolite Trienylfuranol A through Nucleophilic Diastereodivergent Additions to Oxocarbenium Ions

et al. 2021

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Herein, we describe the first total synthesis of trienylfuranol A, a fungal triene-substituted tetrahydrofuran metabolite. The stereoselectivity of the chiral center bearing the trienyl side chain was diastereodivergently controlled by the addition of nucleophilic species on substituted γ-butyrolactone. Remarkably, the C-nucleophilic species or hydride addition onto oxocarbenium intermediate leads to the opposite diastereoselectivity reported for Kishi or Woerpel models. The use of Hantzsch ester (HEH) as organic hydride donor has enabled us to obtain the desired stereochemistry. The total synthesis of trienylfuranol A was achieved in 8 steps from acetaldehyde and pyruvic acid.

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The stereochemistry of 2,4- and 2,3-disubstituted-γ-butyrolactones

Cited by 55 publications

References 0 publications

Algicidal lactones from the marine Roseobacter clade bacterium Ruegeria pomeroyi

Algicidal lactones from the marine Roseobacter clade bacterium Ruegeria pomeroyi

4-Methylthio-2-phthalimido-γ-butyrolactone

Total Synthesis of the Fungal Metabolite Trienylfuranol A through Nucleophilic Diastereodivergent Additions to Oxocarbenium Ions

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