51311-41-2Relevant articles and documents
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
Sarkale, Abhijeet M.,Kumar, Amit,Appayee, Chandrakumar
, p. 4167 - 4172 (2018/04/14)
(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
Replication of biosynthetic reactions enables efficient synthesis of A-factor, a γ-butyrolactone autoinducer from Streptomyces griseus
Morin, Jesse B.,Adams, Katherine L.,Sello, Jason K.
supporting information; experimental part, p. 1517 - 1520 (2012/03/22)
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.
Asymmetric synthesis of A-factor
Crawforth, James M.,Fawcett, John,Rawlings, Bernard J.
, p. 1721 - 1725 (2007/10/03)
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.
Synthesis of Optically Active A-Factor
Parsons, Philip J.,Lacrouts, Pierre,Buss, A. D.
, p. 437 - 438 (2007/10/02)
(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.
Regioselective synthesis of hydroxy butenolides: A convenient synthesis of A-factor
Yadav,Valluri,Rama Rao
, p. 3609 - 3612 (2007/10/02)
An elegant approach for the regioselective preparation of hydroxy butenolide by the oxidation of 2-ethoxyfuran with MnO2-HCl is described.
A Synthesis of 3-Hydroxymethyl-2-(6-methylheptanoyl)-4-butanolide (A-Factor)
Kinoshita, Takamasa,Hirano, Madoka
, p. 1025 - 1026 (2007/10/02)
The A-Factor was conveniently synthesized from 3-furoic acid via the Birch reduction.
Synthetic Microbial Chemistry, XXIII Synthesis of Optically Active Virginiae Butanolides A, B, C, and D and other Autoregulators from Streptomycetes
Mori, Kenji,Chiba, Naoki
, p. 31 - 37 (2007/10/02)
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
ASYMMETRIC CONJUGATE ADDITIONS OF AN HYDROXYMETHYL CARBANION EQUIVALENT. SYNTHESIS OF (+)-A FACTOR
Posner, Gary H.,Weitzberg, Moshe,Jew, Sang-sup
, p. 611 - 620 (2007/10/02)
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.
SYNTHESIS OF OPTICALLY ACTIVE FORMS OF A-FACTOR, THE INDUCER OF STREPTOMYCIN BIOSYNTHESIS IN INACTIVE MUTANTS OF STREPTOMYCES GRISEUS
Mori, Kenji,Yamane, Kazusuke
, p. 2919 - 2921 (2007/10/02)
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.
