88526-08-3Relevant academic research and scientific papers
Cyclopentane construction with control of side chain configuration synthesis of (+)-brefeldin A
Taber, Douglas F.,Silferberg, Lee J.,Robinson, Edward D.
, p. 6639 - 6645 (2007/10/02)
Intramolecular opening of an enantiomerically pure epoxide by an amide enolate (1 → 2) is shown to be an effective method for cyclopentane construction with control of both ring and side chain absolute configuration. This opening serves as the key step in a synthesis of the Golgi apparatus-blocking macrolide (+)-brefeldin A (3). Other features of the synthesis include improved procedures for the enantioselective hydrogenation of a β-keto ester to the corresponding β-hydroxy ester, and for the Julia-Lythgoe reduction of a β-acetoxy sulfone to the trans alkene.
Stereochemical control in microbial reduction. 12. (S)-4-nitro-2-butanol as a source to synthesize natural products
Nakamura,Kitayama,Inoue,Ohno
, p. 91 - 96 (2007/10/02)
(S)-(+)-4-Nitro-2-butanol (1) obtained by the stereoselective reduction of 4-nitro-2-butanone by bakers' yeast was employed for the syntheses of natural products. A precursor of (+)-brefeldin A is synthesized starting from this chiral building block by 10 steps short-cut procedure compared with the shortest method so far reported. (S)-(+)-Sulcatol is obtained in much better enantiomeric purity than those reported. The reactivity of 1 in base-catalyzed condensations with Michael acceptors or aldehydes is largely affected by a base employed as the catalyst.
