Asymmetric synthesis of the four possible fagomine isomers.
The asymmetric synthesis of fagomine and its congeners 1-4 has been achieved by catalytic ring-closing metathesis (RCM). The synthesis involved the construction of the piperidene-type chiral building block 5 followed by dihydroxylation, starting from the d-serine-derived Garner aldehyde 6.
Takahata
Hiroki
H
Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, Sendai 981-8558, Japan. takahata@tohoku-pharm.ac.jp
Banba
Yasunori
Y
Ouchi
Hidekazu
H
Nemoto
Hideo
H
Kato
Atsushi
A
Adachi
Isao
I
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006900:Hydroxylation; D050112:Imino Pyranoses; D007202:Indicators and Reagents; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D050112:Imino Pyranoses; D007202:Indicators and Reagents; D010880:Piperidines; C105643:fagomine