TOTAL SYNTHESIS OF (+)-LACTACYSTIN

Authors
NAGAMITSU T SUNAZUKA T TANAKA H OMURA S SPRENGELER PA SMITH AB
Citation
T. Nagamitsu et al., TOTAL SYNTHESIS OF (+)-LACTACYSTIN, Journal of the American Chemical Society, 118(15), 1996, pp. 3584-3590
Citations number
51
Categorie Soggetti
Chemistry
Journal title
Journal of the American Chemical Society → ACNP
ISSN journal
00027863
Volume
118
Issue
15
Year of publication
1996
Pages
3584 - 3590
Database
ISI
SICI code
0002-7863(1996)118:15<3584:TSO(>2.0.ZU;2-R
Abstract
A total synthesis of the novel neurotrophic agent (+)-lactacystin (1) has been achieved in 11 steps and 14% overall yield from (2R,3S)-3-hyd roxyleucine [(+)-16]. The construction and bioassay of several active analogs are also described. A new asymmetric approach furnished the fo ur stereoisomers of 3-hydroxyleucine, as required starting materials i n high overall yield and enantiomeric purity.