155975-72-7Relevant articles and documents
Structure-activity relationships of lactacystin, the first non-protein neurotrophic factor [6]
Nagamitsu,Sunazuka,Stump,Obata,Arima,Matsuzaki,Tanaka,Omura
, p. 747 - 748 (1995)
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An efficient synthesis of lactacystin β-lactone
Donohoe, Timothy J.,Sintim, Herman O.,Sisangia, Leena,Harling, John D.
, p. 2293 - 2296 (2004)
A key step in the synthesis of lactacystin β-lactone (3), an inhibitor of the 20 S proteasome, was the ammonia-free reductive aldol reaction of pyrrole 1 to form 2 with complete anti selectivity. This route to 3 takes just 13 steps (14% overall yield) and allows the late-stage stereoselective introduction of a methyl group at C4, which is crucial for the production of analogues. Boc = tert-butoxycarbonyl.
Application of Two Direct C(sp3)-H Functionalizations for Total Synthesis of (+)-Lactacystin
Yoshioka, Shun,Nagatomo, Masanori,Inoue, Masayuki
, p. 90 - 93 (2015/07/28)
(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.
Enantioselective total syntheses of omuralide, 7-epi-omuralide, and (+)-lactacystin
Hayes, Christopher J.,Sherlock, Alexandra E.,Green, Martin P.,Wilson, Claire,Blake, Alexander J.,Selby, Matthew D.,Prodger, Jeremy C.
, p. 2041 - 2051 (2008/09/19)
(Chemical Equation Presented) An alkylidene carbene 1,5-CH insertion has been used as a key step in an enantioselective total syntheses of omuralide, its C7-epimer, and (+)-lactacystin. An additional noteworthy feature of the synthesis is the use of a nov