Asymmetric total synthesis of (+)-swainsonine.
A concise asymmetric synthesis of (+)-swainsonine (ent-1) is described starting from 2, which was readily prepared from commercially available l-glutamic acid. The method features installation of the indolizidine ring via an intramolecular cyclisation of α-sulfinyl carbanion as a key step. (+)-Swainsonine was obtained in 11.8% overall yield in 10 steps.
Chooprayoon
Soontorn
S
Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok, 10400, Thailand.
Kuhakarn
Chutima
C
Tuchinda
Patoomratana
P
Reutrakul
Vichai
V
Pohmakotr
Manat
M
D018698:Glutamic Acid / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D017026:Swainsonine / Q000138:chemical synthesis*
D018698:Glutamic Acid; D017026:Swainsonine