Found 2 publications. Displayed publications from 1 to 2
Expand all publications       Show all as text (SweetDB notation)
1. (Article ID: 5558)
 
Glaus F, Altmann KH
Total synthesis of the tiacumicin B (lipiarmycin A3/fidaxomicin) aglycone
Angewandte Chemie, International Edition 54(6) (2015) 1937-1940
 

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

synthesis, Mycobacterium tuberculosis, Clostridium difficile, tiacumicin, Dactylosporangium aurantiacum

The publication contains the following compound(s):
 

Expand this publication
2. (Article ID: 5578)
 
Miyatake-Ondozabal H, Kaufmann E, Gademann K
Total synthesis of the protected aglycon of fidaxomicin (tiacumicin B, lipiarmycin A3)
Angewandte Chemie, International Edition 54(6) (2015) 1933-1936
 

Fidaxomicin, also known as tiacumicin B or lipiarmycin A3, is a novel macrocyclic antibiotic that is used in hospitals for the treatment of Clostridium difficile infections. This natural product has also been shown to have excellent bactericidal activity against multidrug-resistant Mycobacterium tuberculosis. In spite of its attractive biological activity, no total synthesis has been reported to date. The enantioselective synthesis of the central 18-membered macrolactone is reported herein. The key reactions include ring-closing metathesis between a terminal olefin and a dienoate moiety for macrocyclization, a vinylogous Mukaiyama aldol reaction, and a Stille coupling reaction of sterically demanding substrates. The retrosynthesis involves three medium-sized fragments, thus leading to a flexible yet convergent synthetic route

natural products, antibiotics, cross coupling, stereoselective synthesis

The publication contains the following compound(s):
 

Expand this publication

Resort publications by:

New query Export IDs Home Help

Execution: <1 sec