- Organocatalytic approach for short asymmetric synthesis of (r)-paraconyl alcohol: Application to the total syntheses of IM-2, SCB2, and a-factor γ-butyrolactone autoregulators
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(R)-Paraconyl alcohol is found to be a key intermediate for the syntheses of many γ-butyrolactone autoregulators. The chiral auxiliary approach and enzymatic resolution are the two common strategies employed so far in the literature for the asymmetric syn
- Sarkale, Abhijeet M.,Kumar, Amit,Appayee, Chandrakumar
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p. 4167 - 4172
(2018/04/14)
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- Replication of biosynthetic reactions enables efficient synthesis of A-factor, a γ-butyrolactone autoinducer from Streptomyces griseus
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We report a concise synthesis of A-factor, the prototypical γ-butyrolactone signalling compound of Streptomyces bacteria. In analogy to enzymatic reactions in A-factor biosynthesis, our synthesis features a tandem esterification-Knoevenagel condensation yielding a 2-acyl butenolide and a surprising, chemoselective conjugate reduction of this α,β- unsaturated carbonyl compound using sodium cyanoborohydride.
- Morin, Jesse B.,Adams, Katherine L.,Sello, Jason K.
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supporting information; experimental part
p. 1517 - 1520
(2012/03/22)
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- Asymmetric synthesis of A-factor
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The synthesis of enantlopure A-factor ['autoregulatory factor'; (3R)-(-)-2-(6-methylheptanoyl)-3-hydroxymethylbutano-4-lactone] by the completely diastereoselective benzyloxymethylation of (4R)-3-(3-phenylpropanoyl)-4-isopropyloxazolidin-2-one is reported.
- Crawforth, James M.,Fawcett, John,Rawlings, Bernard J.
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p. 1721 - 1725
(2007/10/03)
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- Synthesis of Optically Active A-Factor
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(3R)-(-)-A-factor and (3S)-(+)-A-factor are synthesised via the same chiral intermediate 6, the synthesis of which proceeds through a Johnson-Claisen rearrangement key step.
- Parsons, Philip J.,Lacrouts, Pierre,Buss, A. D.
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p. 437 - 438
(2007/10/02)
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- Regioselective synthesis of hydroxy butenolides: A convenient synthesis of A-factor
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An elegant approach for the regioselective preparation of hydroxy butenolide by the oxidation of 2-ethoxyfuran with MnO2-HCl is described.
- Yadav,Valluri,Rama Rao
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p. 3609 - 3612
(2007/10/02)
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- A Synthesis of 3-Hydroxymethyl-2-(6-methylheptanoyl)-4-butanolide (A-Factor)
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The A-Factor was conveniently synthesized from 3-furoic acid via the Birch reduction.
- Kinoshita, Takamasa,Hirano, Madoka
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p. 1025 - 1026
(2007/10/02)
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- Synthetic Microbial Chemistry, XXIII Synthesis of Optically Active Virginiae Butanolides A, B, C, and D and other Autoregulators from Streptomycetes
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Optically active A-factor (1), the factor from Streptomyces viridochromogenes (2), the factors from S. bikiniensis and S. cyaneofuscatus (3-5), and virginiae butanolides A (6), B (7), C (8), and D (9) were synthesized starting from (S)-(-)-paraconic acid
- Mori, Kenji,Chiba, Naoki
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- ASYMMETRIC CONJUGATE ADDITIONS OF AN HYDROXYMETHYL CARBANION EQUIVALENT. SYNTHESIS OF (+)-A FACTOR
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An effective procedure is presented for generation of Ph2CH2OCH2Li via tin -> lithium exchange and for conjugate addition of this HOCH2- equivalent to some homochiral cycloalkenone and butenolide sulfoxides.
- Posner, Gary H.,Weitzberg, Moshe,Jew, Sang-sup
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p. 611 - 620
(2007/10/02)
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- SYNTHESIS OF OPTICALLY ACTIVE FORMS OF A-FACTOR, THE INDUCER OF STREPTOMYCIN BIOSYNTHESIS IN INACTIVE MUTANTS OF STREPTOMYCES GRISEUS
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The absolute configuration at C-3 of A-factor, 2-(6-methylheptanoyl)-3-hydroxymethyl-4-butanolide 1a, was determined to be S by synthesizing both enantiomers of it from paraconic acid. (3S)-A-factor was 2.5 times more active than the (3R)-isomer as the inducer of streptomycin biosynthesis in inactive mutants of Streptomyces griseus.
- Mori, Kenji,Yamane, Kazusuke
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p. 2919 - 2921
(2007/10/02)
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