Takahata Hiroki, Banba Yasunori, Ouchi Hidekazu, Nemoto Hideo, Kato Atsushi, Adachi Isao
Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, Sendai 981-8558, Japan.
J Org Chem. 2003 May 2;68(9):3603-7. doi: 10.1021/jo034137u.
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.