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This review describes two novel synthetic routes from (S)-pyroglutaminol to (+)-lactacystin, a potent inhibitor of the 20S proteasome and from d-gluconolactone derivative to zaragozic acid C, a potent squalene synthase inhibitor. In lactacystin synthesis, the photoinduced intermolecular C(sp 3 )-H alkynylation and intramolecular C(sp 3 )-H acylation chemoselectively and stereoselectively constructed the tetrasubstituted and trisubstituted carbon centers, respectively. In the synthesis of zaragozic acid C, the stereoselective installation of the two contiguous tetrasubstituted carbons was achieved by the photochemical intramolecular C(sp 3 )-H acylation of a densely oxygenated intermediate.

yakugaku zasshi

Development of Synthetic Strategies for Densely Oxygenated Natural Products: Total Synthesis of Lactacystin and Zaragozic Acid C Using Photochemical C(sp&lt;sup&gt;3&lt;/sup&gt;)-H Functionalization