SEMINARIO QUÍMICA ORGÁNICA 10-08-20
TÍTULO: "Synthesis of Islatravir Enabled by a Catalytic, Enantioselective Alkynylation of a Ketone"
FUENTE: Niki R. Patel, Christopher C. Nawrat, Mark McLaughlin, Yingju Xu, Mark A. Huffman, Hao Yang, Hongming Li, Aaron M. Whittaker, Teresa Andreani, François Lévesque, Anna Fryszkowska, Andrew Brunskill, David M. Tschaen, and Kevin M. Maloney. Organic Letters 2020, 12, 4659-4664..
EXPOSITOR: Lic. Carmela A. Crespo Guridi
DÍA, HORA y LUGAR: Lunes 10 de agosto de 2020, 18:00 h, Plataforma MEET GOOGLE.
Link: meet.google.com/pst-wjwm-pzs
RESUMEN:
The synthesis of the potent anti-HIV investigational treatment islatravir is described. The key step in this synthesis is a highly enantioselective catalytic asymmetric alkynylation of a ketone. This reaction is a rare example of the asymmetric addition of an alkyne nucleophile to a ketone through ligand-accelerated catalysis that was performed on a greater than 100 g scale. By leveraging a multienzyme cascade, a highly diastereoselective aldol-glycosylation was used to complete the target in eight steps.
TÍTULO: "Synthesis of Islatravir Enabled by a Catalytic, Enantioselective Alkynylation of a Ketone"
FUENTE: Niki R. Patel, Christopher C. Nawrat, Mark McLaughlin, Yingju Xu, Mark A. Huffman, Hao Yang, Hongming Li, Aaron M. Whittaker, Teresa Andreani, François Lévesque, Anna Fryszkowska, Andrew Brunskill, David M. Tschaen, and Kevin M. Maloney. Organic Letters 2020, 12, 4659-4664..
EXPOSITOR: Lic. Carmela A. Crespo Guridi
DÍA, HORA y LUGAR: Lunes 10 de agosto de 2020, 18:00 h, Plataforma MEET GOOGLE.
Link: meet.google.com/pst-wjwm-pzs
RESUMEN:
The synthesis of the potent anti-HIV investigational treatment islatravir is described. The key step in this synthesis is a highly enantioselective catalytic asymmetric alkynylation of a ketone. This reaction is a rare example of the asymmetric addition of an alkyne nucleophile to a ketone through ligand-accelerated catalysis that was performed on a greater than 100 g scale. By leveraging a multienzyme cascade, a highly diastereoselective aldol-glycosylation was used to complete the target in eight steps.
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