135191-49-0Relevant academic research and scientific papers
Enantioselective Synthesis of (+)-Brefeldin A
Solladie, Guy,Lohse, Olivier
, p. 4555 - 4563 (1993)
A new enantioselective synthesis of (+)-brefeldin A is described.The five chiral centers are created by the following methodology: asymmetric Diels-Alder reaction to prepare the cyclopentanone 13, stereocontrolled reduction of the carbonyl in the ketone 14, stereocontrolled creation of the chiral centers C-4 and C-15 by a chiral sulfoxide group.
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.
