Synthesis of β-methoxyacrylate natural products based on box-Pd(II)-catalyzed intermolecular methoxycarbonylation of alkynoles.
Bis(oxazoline)-palladium(II) catalyzed carbonylation of homopropargyl alcohols afforded acyclic methoxyacrylate 2 and 6-membered lactone 3a-k in good combined yield. In the case of propargyl alcohols, 5-membered lactones 3p, 3q, 16 were obtained in moderate yields. The one-pot synthesis of kawa lactones 3a, 3r, 3s and formal synthesis of dihydroxycystothiazole A and dihydroxycystothiazole C are presented. To elucidate the stereochemistry of (+)-annularin G and (-)-annularin H, the first asymmetric syntheses of these natural products were achieved.
Motodate
Satoshi
S
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan.
Kobayashi
Takuya
T
Fujii
Mikio
M
Mochida
Tomoyuki
T
Kusakabe
Taichi
T
Katoh
Shigeki
S
Akita
Hiroyuki
H
Kato
Keisuke
K
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000179:Acrylates / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
C555041:4-methoxy-5-(2-hydroxybutyl)-2,(5H)-furanone; C555042:4-methoxy-5-(2-oxobutyl)-2,(5H)-furanone; D000179:Acrylates; D001688:Biological Products; D007783:Lactones; D010165:Palladium; D015107:4-Butyrolactone