135191-50-3Relevant academic research and scientific papers
Enantioselective formal synthesis of brefeldin A and analogues via anionic cyclization of an alkenyl epoxide
Hübscher, Tina,Helmchen, Günter
, p. 1323 - 1326 (2007/10/03)
Cyclopentene derivatives suitable as intermediates for syntheses of brefeldin A and analogues 6,7-dehydrobrefeldin C and norbrefeldin A were prepared by epoxynitrile cyclization of alkenyl epoxides. Georg Thieme Verlag Stuttgart.
Stereocontrolled Synthesis of Dihydroxycyclopentane Derivative: Enantioselective Synthesis of (+)-Brefeldin A
Miyaoka, Hiroaki,Kajiwara, Masahiro
, p. 483 - 484 (2007/10/02)
A novel enantioselective synthesis of (+)-brefeldin A was achieved via stereocontrolled one-pot synthesis of a dihydroxycyclopentane derivative from allyl phenyl sulfone and chiral diepoxide.
One-pot synthesis of dihydroxycyclopentanes from allylsulfones and chiral diepoxides
Miyaoka,Kajiwara
, p. 1659 - 1661 (2007/10/02)
Allylphenylsulfonyl lithium, generated from allyl phenyl sulfone and (n)BuLi, reacts with chiral diepoxides to give dihydroxycyclopentane derivatives in good yields. The synthesis of the aldehyde 2, which is a key intermediate for brefeldin A, was achieve
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.
