Synthesis of the antimalarial drug FR900098 utilizing the nitroso-ene reaction.
The antimalarial drug FR900098 was prepared from diethyl allylphosphonate involving the nitroso-ene reaction with nitrosocarbonyl methane as the key step followed by hydrogenation and dealkylation. The utilization of dibenzyl allylphosphonate as the starting compound allows one-step hydrogenation with dealkylation, which simplifies the preparative scheme further.
Fokin
Andrey A
AA
Department of Organic Chemistry, Kiev Polytechnic Institute, pr. Pobedy 37, 03056 Kiev, Ukraine. aaf@xtf.ntu-kpi.kiev.ua
Yurchenko
Alexander G
AG
Rodionov
Vladimir N
VN
Gunchenko
Pavel A
PA
Yurchenko
Raisa I
RI
Reichenberg
Armin
A
Wiesner
Jochen
J
Hintz
Martin
M
Jomaa
Hassan
H
Schreiner
Peter R
PR
D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005578:Fosfomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006865:Hydrogenation; D015394:Molecular Structure; D009603:Nitroso Compounds / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000962:Antimalarials; D009603:Nitroso Compounds; D063065:Organophosphonates; D005578:Fosfomycin; C024639:3-(N-acetyl-N-hydroxy)aminopropylphosphonic acid