1354939-16-4Relevant articles and documents
Total synthesis and biological evaluation of pacidamycin D and its 3′-hydroxy analogue
Okamoto, Kazuya,Sakagami, Masahiro,Feng, Fei,Togame, Hiroko,Takemoto, Hiroshi,Ichikawa, Satoshi,Matsuda, Akira
, p. 1367 - 1377 (2012/03/27)
Full details of the total synthesis of pacidamycin D (4) and its 3′-hydroxy analogue 32 are described. The chemically labile Z-oxyacyl enamide moiety is the most challenging chemical structure found in uridylpeptide natural products. Key elements of our approach to the synthesis of 4 include the efficient and stereocontrolled construction of the Z-oxyvinyl halides 6 and 7 and their copper-catalyzed cross-coupling with the tetrapeptide carboxamide 5, a thermally unstable compound containing a number of potentially reactive functional groups. This synthetic route also allowed us to easily prepare 3′-hydroxy analogue 32. The assemblage by cross-coupling of the Z-oxyvinyl halide 6 and the carboxamide 5 at a late stage of the synthesis provided ready access to a range of uridylpeptide antibiotics and their analogues, despite their inherent labile nature with potential epimerization, simply by altering the tetrapeptide moiety.
