73899-78-2Relevant academic research and scientific papers
A Short Synthesis of (+)-Brefeldin C through Enantioselective Radical Hydroalkynylation
Gn?gi, Lars,Martz, Severin Vital,Meyer, Daniel,Sch?rer, Robin Marc,Renaud, Philippe
supporting information, p. 11646 - 11649 (2019/08/30)
A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows a high trans diastereoselectivity to be achieved during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis requires six product purifications and it provides (+)-brefeldin C in 18 % overall yield.
Total synthesis of (+)-brefeldin c utilizing aza-Claisen rearrangement
Inai, Makoto,Nishii, Takeshi,Mukoujima, Shingo,Esumi, Tomoyuki,Kaku, Hiroto,Tominaga, Keiko,Abe, Hiroaki,Horikawa, Mitsuyo,Tsunoda, Tetsuto
scheme or table, p. 1459 - 1461 (2011/07/30)
The total synthesis of (+)-brefeldin C was accomplished. An asymmetric aza-Claisen rearrangement developed by our laboratory was employed to construct the C-4 and C-5 stereogenic centers of (+)-brefeldin C as a key step. Georg Thieme Verlag Stuttgart - New York.
Total synthesis of (+)-brefeldin C, (+)-nor-Me brefeldin A and (+)-4-epi-nor-Me brefeldin A
Archambaud, Sylvie,Legrand, Frederic,Aphecetche-Julienne, Karine,Collet, Sylvain,Guingant, Andre,Evain
experimental part, p. 1364 - 1380 (2010/05/03)
A total synthesis of (+)-brefeldin C (BFC) and two brefeldin A (BFA) analogues - (+)-nor-Me BFA and (+)-4-epi-nor-Me BFA - has been developed. Key features of the syntheses include desymmetrization of meso anhydrides, a Carreira reaction to control the ab
A new total synthesis of (+)-brefeldin C
Archambaud, Sylvie,Aphecetche-Julienne, Karine,Guingant, André
, p. 139 - 143 (2007/10/03)
A new synthesis of (+)-brefeldin C featuring a Bolm desymmetrisation reaction, a B-alkyl Suzuki-Miyaura cross-coupling and a Carreira alkynylation reaction as the key steps is reported.
