Abstract
The chiral and stereoselective synthesis of (+)-lactacystin 1, the first non-protein neurotrophic factor having an α,α-disubstituted α- amino acid structure, is described. The highly functionalized γ- lactam portion possessing a tetra-substituted carbon with nitrogen in 1 was effectively constructed from D-glucose using allylic trichloroacetimidate rearrangement (Overman rearrangement) as the key reaction.
| Original language | English |
|---|---|
| Pages (from-to) | 16287-16298 |
| Number of pages | 12 |
| Journal | Tetrahedron |
| Volume | 53 |
| Issue number | 48 |
| DOIs | |
| Publication status | Published - 1997 Dec 1 |
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ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Stereoselective total synthesis of (+)-lactacystin from D-glucose. / Chida, Noritaka; Takeoka, Jun; Ando, Kohji; Tsutsumi, Noriko; Ogawa, Seiichiro.
In: Tetrahedron, Vol. 53, No. 48, 01.12.1997, p. 16287-16298.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Stereoselective total synthesis of (+)-lactacystin from D-glucose
AU - Chida, Noritaka
AU - Takeoka, Jun
AU - Ando, Kohji
AU - Tsutsumi, Noriko
AU - Ogawa, Seiichiro
PY - 1997/12/1
Y1 - 1997/12/1
N2 - The chiral and stereoselective synthesis of (+)-lactacystin 1, the first non-protein neurotrophic factor having an α,α-disubstituted α- amino acid structure, is described. The highly functionalized γ- lactam portion possessing a tetra-substituted carbon with nitrogen in 1 was effectively constructed from D-glucose using allylic trichloroacetimidate rearrangement (Overman rearrangement) as the key reaction.
AB - The chiral and stereoselective synthesis of (+)-lactacystin 1, the first non-protein neurotrophic factor having an α,α-disubstituted α- amino acid structure, is described. The highly functionalized γ- lactam portion possessing a tetra-substituted carbon with nitrogen in 1 was effectively constructed from D-glucose using allylic trichloroacetimidate rearrangement (Overman rearrangement) as the key reaction.
UR - http://www.scopus.com/inward/record.url?scp=0030776124&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0030776124&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(97)01015-6
DO - 10.1016/S0040-4020(97)01015-6
M3 - Article
VL - 53
SP - 16287
EP - 16298
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 48
ER -