Synthesis of Squamostanal-A.
The first synthesis of squamostanal-A (1), separated as a degradation product of tetrahydrofuranic acetogenins, is described. Iodide 7, which corresponds to the latent aldehyde moiety of 1, was prepared through a 2-step sequence from 13-[tetrahydropyran-2'- yloxy]-2-tridecyn-l-ol (5). The NaHMDS-based coupling reaction of 7 with γ-lactone 8 gave compound 9, which by a 3-step sequence, was coverted to 1.
a Department of Applied Biological Chemistry, Faculty of Agriculture , Graduate School of Agriculture, Tohoku University, 1-1 Tsutsumidori Amamiyamachi , Aoba-ku, Sendai 981 , Japan.
H
H
Konno
a Department of Applied Biological Chemistry, Faculty of Agriculture , Graduate School of Agriculture, Tohoku University, 1-1 Tsutsumidori Amamiyamachi , Aoba-ku, Sendai 981 , Japan.
H
H
Makabe
a Department of Applied Biological Chemistry, Faculty of Agriculture , Graduate School of Agriculture, Tohoku University, 1-1 Tsutsumidori Amamiyamachi , Aoba-ku, Sendai 981 , Japan.|b Division of Environmental Bioremediation, Graduate School of Agriculture , Graduate School of Agriculture, Tohoku University, 1-1 Tsutsumidori Amamiyamachi , Aoba-ku, Sendai 981 , Japan.
A
A
Tanaka
a Department of Applied Biological Chemistry, Faculty of Agriculture , Graduate School of Agriculture, Tohoku University, 1-1 Tsutsumidori Amamiyamachi , Aoba-ku, Sendai 981 , Japan.
T
T
Oritani
annonaceous acetogenins; oxidative cleavage