- (+/-)-erythro-γ,δ-Dihydroxycarboxylic Acid Lactones from a β-Lithiopropionate Equivalent and α-Chloroaldehydes
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Reaction of β-ethylthio-β-lithioacrylate 1A with α-chloroaldehydes furnished predominantly the erythro products 3, which were isolated as γ-lactones 4.At room temperature intermediates 3 are transformed into the (+/-)-erythro-γ,δ-dihydroxycarboxylic acid γ-lactones 8.Raney nickel treatment provided interesting natural γ-lactone derivatives; thus, from erythro-8c the socalled L-factor erythro-9c was obtained.Similarly, from β-methoxy β-lithioacrylate 10A the (+/-)-erythro-γ,δ-dihydroxycarboxylic acid δ-lactone erythro-11 was gained.
- Plewe, Michael,Schmidt, Richard R.
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p. 534 - 536
(2007/10/02)
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- A Simple, General Diastereoselective Synthesis of 5-Hydroxyalkylbutan-4-olides
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cis- and trans-Hex-4-enoic acids and their 6-n-propyl and n-butyl derivatives, when treated with a 1.1 molar excess of m-chloroperbenzoic acid and Amberlyst-15 as catalyst in CH2Cl2 at 20 deg C, gave the corresponding threo- and erythro-5-hydroxyalkylbutan-4-olides in quantitative yields.
- Jefford, Charles W.,Wang, Ying
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p. 1513 - 1514
(2007/10/02)
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