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Stereoselective total synthesis of (+)-lactacystin from d-glucose

✍ Scribed by Noritaka Chida; Jun Takeoka; Kohji Ando; Noriko Tsutsumi; Seiichiro Ogawa

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 776 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)01015-6

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✦ Synopsis

The chiral and stereoselective synthesis of (+)-lactacystin 1, the first non-protein neurotrophic factor having an ct,~t-disubstituted a-amino acid structure, is described. The highly functionalized y-lactam portion possessing a tetra-substituted carbon with nitrogen in I was effectively constructed from D-glucose using allylic trichloroacetimidate rearrangement (Overman rearrangement) as the key reaction.

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