Facile and efficient synthesis of lactols by a domino reaction of 2,3-epoxy alcohols with a hypervalent iodine(III) reagent and its application to the synthesis of lactones and the asymmetric synthesis of (+)-tanikolide.
The domino reaction of 2,3-epoxy-1-alcohol derivatives, namely tetrasubstituted 2,3-epoxy-1-alcohols and 2- or 3-alkyl trisubstituted 2,3-epoxy-1-alcohols, with PhI(OCOCF(3))(2) in the presence of H(2)O is described in detail. In this reaction, several types of lactol derivatives can be directly obtained from the 2,3-epoxy-1-alcohol derivatives in a single operation. The obtained lactols were successively converted into the corresponding lactones. This reaction is applicable to the construction of optically active lactone compounds. The asymmetric total synthesis of (+)-tanikolide, an antifungal marine natural product, has been effectively achieved by using this reaction.
Fujioka
Hiromichi
H
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan.
Matsuda
Satoshi
S
Horai
Mai
M
Fujii
Eri
E
Morishita
Maiko
M
Nishiguchi
Natsuko
N
Hata
Kayoko
K
Kita
Yasuyuki
Y
D000438:Alcohols / Q000737:chemistry*; D000935:Antifungal Agents / Q000138:chemical synthesis*; D001688:Biological Products / Q000138:chemical synthesis*; D004852:Epoxy Compounds / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis*; D008386:Marine Biology; D008956:Models, Chemical; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
D000438:Alcohols; D000935:Antifungal Agents; D001688:Biological Products; D004852:Epoxy Compounds; D007783:Lactones; C400156:tanikolide; D014867:Water; D007455:Iodine