- Total synthesis of (±)-pentenomycin
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A concise stereoselective route to (±)-pentenomycin 1 in 33% overall yield starting from the readily accessible Diels-Alder adduct 4 is reported. The key reaction involves decarbonylation of β-methoxy-α,β-unsaturated aldehyde 8 obtained from β-hydroxy-dimethylketal 6.
- Khan, Faiz Ahmed,Rout, Bhimsen
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p. 5251 - 5253
(2007/10/03)
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- Intramolecular acylation of α-sulfinyl carbanion: A facile synthesis of (±)-pentenomycin I and (±)-epipentenomycin I
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(±)-Pentenomycin I and (±)-epipentenomycin I were synthesized, starting from methyl 2,2-dimethyl-1,3-dioxolane-4-carboxylate. The key reaction involved the intramolecular acylation of α-sulfinyl carbanion and pyrolysis of the resulting product.
- Pohmakotr,Popuang
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p. 275 - 278
(2007/10/02)
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- Studies Related to Cyclopentanoid Natural Products. Part 3. Synthesis of Pentenomycin and its Racemate
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(4R)-4-Benzyloxy-2-benzyloxymethylcyclopent-2-en-1-one (9b) reacted with osmium(VIII) oxide to give (2S,3S,4R)-4-benzyloxy-2-benzyloxymethyl-2,3-dihydroxycyclopentan-1-one (8b), the cis-hydroxylation occurring anti to the 4-benzyloxy group.By a hydrogenolysis-dehydration sequence, compound (8b) was converted into pentenomycin (1a).Although the optical rotations of the synthetic pentenomycin (1a) and its 4,5,6-tri-O-acetyl, 2-bromo-4,5,6-tri-O-acetyl, and 6-O-benzyl derivatives (13a), (13b), and (1d), were substantially different from those reported in the literature, the compounds were shown to be enantiomerically pure.When treated with t-butyldimethylsilyl chloride, (8R)-8-hydroxy-6-hydroxymethyl-1,4-thiaspiro-non-6-ene (10b) was converted into its disilyl ether (10f).The last-cited compound reacted with benzeneseleninic anhydride to give (4R)-4-t-butyldimethylsilyloxy-2-t-butyldimethylsilyloxymethylcyclopent-2-en-1-one (9d), which was converted into pentenomycin (1a) by sequential reactions involving osmium(VIII) oxide and hydrochloric acid.The racemate of compound (9d), prepared from the racemate of 4-hydroxy-2-hydroxymethylcyclopent-2-en-1-one (9c) by reaction with t-butyldimethylsilyl chloride, was similarly transformed into the racemate of pentenomycin (1a).
- Hetmanski, Michael,Purcell, Neil,Stoodley, Richard J.,Palfreyman, Malcolm N.
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p. 2089 - 2096
(2007/10/02)
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- Syntheses of (±)-and (-)-pentenomycin I
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Syntheses of the cyclopentanoid antibiotic. (-)-pentenomycin I, from D-(-)-quinic acid are described; (±)-pentenomycin I is also prepared from 3-hydroxymethyl-2-methylfuran.
- Elliott,Hetmanski,Palfreyman,et al.
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p. 965 - 968
(2007/10/02)
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