Stereocontrolled total synthesis of potent immunosuppressant FR901483.
A total synthesis of the potent immunosuppressant FR901483 (1) has been accomplished. The key feature of our convergent synthesis is the stereoselective incorporation of the p-methoxybenzyl and methylamino groups within the core moiety 10. Tricycle 10 was itself constructed by an intramolecular aldol reaction of the symmetrical keto-aldehyde 7. [Structure: see text]
Kan
Toshiyuki
T
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Fujimoto
Teppei
T
Ieda
Shigeru
S
Asoh
Yusuke
Y
Kitaoka
Haruka
H
Fukuyama
Tohru
T
D000447:Aldehydes / Q000737:chemistry; D000478:Alkylation; D001203:Ascomycota; D007166:Immunosuppressive Agents / Q000138:chemical synthesis*; D008744:Methylamines / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis*
D000447:Aldehydes; C098358:FR 901483; D007166:Immunosuppressive Agents; D008744:Methylamines; D009943:Organophosphorus Compounds; C116609:3-hydroxybutanal; C027451:methylamine