928209-78-3Relevant academic research and scientific papers
Application of Two Direct C(sp3)-H Functionalizations for Total Synthesis of (+)-Lactacystin
Yoshioka, Shun,Nagatomo, Masanori,Inoue, Masayuki
, p. 90 - 93 (2015)
(Figure Presented). Herein, we report a new synthetic route from (S)-pyroglutaminol to (+)-lactacystin, a potent inhibitor of the 20S proteasome. The photoinduced intermolecular C(sp3)-H alkynylation and intramolecular C(sp3)-H acylation chemo- and stereoselectively constructed the tetra- and trisubstituted carbon centers, respectively. The obtained bicycle was transformed into the target compound in a concise manner. The present total synthesis demonstrates the power of the direct C(sp3)-H functionalizations for the assembly of multiple functionalized structures of natural products.
