Syntheses of hydantocidin and C-2-thioxohydantocidin.
Hydantocidin (12), a naturally occurring strong herbicide, was synthesized in 35.2% overall yield, with accompanying 5-epi-hydantocidin (12') in 9.6% overall yield via isothiocyanate (13) and spiro-hydantoin (10) from 2,3-O-isopropylidene-D-ribono-1,4-lactone (1). C-2-thioxo-hydantocidin (24) was also synthesized in 16.5% overall yield with accompanying 5-epi-C-2-thioxohydantocidin (24', 9.2% yield) via isothiocyanate (22).
Shiozaki
Masao
M
Exploratory Chemistry Research Laboratories, Sankyo Co, Ltd, Hiromachi 1-2-58, Shinagawa-ku, Tokyo 140-8710, Japan. shioza@shina.sankyo.co.jp
D006540:Herbicides / Q000138:chemical synthesis; D006827:Hydantoins / Q000138:chemical synthesis*; D017879:Isothiocyanates / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
C441248:C-2-thioxo-hydantocidin; D006540:Herbicides; D006827:Hydantoins; D017879:Isothiocyanates; D007783:Lactones; C068815:hydantocidin; C037152:isothiocyanic acid