546084-44-0Relevant articles and documents
Total synthesis of the Tiacumicin B (lipiarmycin A3/fidaxomicin) aglycone
Glaus, Florian,Altmann, Karl-Heinz
, p. 1937 - 1940 (2015)
Tiacumicin B (lipiarmycin A3, fidaxomicin) is an atypical macrolide antibiotic which is used for the treatment of Clostridium difficile infections. Tiacumicin B is also a potent inhibitor of Mycobacterium tuberculosis, but due to its limited oral bioavailability is unsuitable for systemic therapy. To provide a basis for structure-activity studies that might eventually lead to improved variants of tiacumicin B, we have developed an efficient approach to the synthesis of the tiacumicin B aglycone. The synthesis features a high-yielding intramolecular Suzuki cross-coupling reaction to effect macrocyclic ring closure. Key steps in the synthesis of the macrocyclization precursor were a highly selective, one-pot Corey-Peterson olefination and an ene-diene cross-metathesis reaction. Depending on the reaction conditions, the final deprotection delivered either the fully deprotected tiacumicin B aglycone or partially protected versions thereof.
Total Synthesis of (-)-Disorazole C1
Lizzadro, Luca,Spie?, Oliver,Schinzer, Dieter
supporting information, p. 4543 - 4547 (2021/06/28)
Disorazoles represent a powerful class of highly potent antitubulin natural products isolated from myxobacteria. Herein, we describe a scalable and robust synthesis of (-)-disorazole C1 with high stereoselectivity, featuring quite simple reaction conditio
Chiral hybrid silica: Sol-gel heterogenisation of trans-(1R,2R)- diaminocyclohexane ligands for the rhodium catalysed enantioselective reduction of acetophenone
Brethon, Anne,Moreau, Joel J.E.,Man, Michel Wong Chi
, p. 495 - 502 (2007/10/03)
The synthesis of derivatives of trans-(1R,2R)-diaminocyclohexane with different substituents on the nitrogen atoms has been achieved. Rhodium complexes of these chiral ligands were evaluated as homogeneous catalysts for the asymmetric hydride transfer red