Total synthesis of (-)-stellettamide B and determination of its absolute stereochemistry.
[figure: see text] The first total synthesis of (-)-stellettamide B has been achieved by a sequence based on amide coupling of the chiral 1-(aminomethyl)-indolizidine fragment, prepared by TiCl4-mediated asymmetric allylation of the tricyclic N-acyl-N,O-acetal, with the chiral trienoic acid fragment. This synthesis led to revision of the published relative stereochemistry of the natural product and established its absolute stereochemistry to be 1S,4S,8aR,6"R.
Yamazaki
N
N
School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Dokoshi
W
W
Kibayashi
C
C
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D000470:Alkaloids; D000935:Antifungal Agents; D007202:Indicators and Reagents; C107774:stellettamide B