The efficient direct synthesis of N,O-acetal compounds as key intermediates of discorhabdin A: oxidative fragmentation reaction of alpha-amino acids or beta-amino alcohols by using hypervalent iodine(III) reagents.
Hypervalent iodine(III) reagents are readily available, easy to handle, and have a low toxicity and similar reactivities to those of heavy metal reagents, and hence they are used for various oxidative reactions. The oxidative cleavage of alkynes or carbonyl compounds by using bis(trifluoroacetoxy)iodo(III) pentafluorobenzene (C(6)F(5)I(OCOCF(3))(2)) has been reported. Herein, the efficient direct synthesis of N,O-acetal compounds as key intermediates of discorhabdin A, by the oxidative fragmentation reaction of alpha-amino acids or beta-amino alcohols by using C(6)F(5)I(OCOCF(3))(2), is described.
Harayama
Yu
Y
Graduate School of Pharmaceutical Sciences, Osaka University, Suita, Osaka, 565-0871, Japan.
Yoshida
Masako
M
Kamimura
Daigo
D
Wada
Yasufumi
Y
Kita
Yasuyuki
Y
D000596:Amino Acids / Q000737:chemistry*; D000605:Amino Alcohols / Q000737:chemistry*; D002384:Catalysis; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D011809:Quinones / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013841:Thiazepines / Q000138:chemical synthesis*; D005464:Fluorobenzenes; D005466:Fluorocarbons; D006847:Hydrocarbons, Iodinated
D000596:Amino Acids; D000605:Amino Alcohols; D006846:Hydrocarbons, Halogenated; D011809:Quinones; D013141:Spiro Compounds; D013841:Thiazepines; C521471:bis(trifluoroacetoxy)iodo(III) pentafluorobenzene; D005464:Fluorobenzenes; D005466:Fluorocarbons; D006847:Hydrocarbons, Iodinated; C471812:discorhabdin A