Determination of the absolute structure of (+)-akaterpin.
We describe the total synthesis and structural determination of (+)-akaterpin (1), an inhibitor of phosphatidylinositol-specific phospholipase C (PI-PLC). The key features of the synthetic strategy include the resolution of β,γ-unsaturated ketone (±)-2a with chiral sulfoximine 6. The absolute stereochemistry was determined by comparison of the specific optical rotation data of (+)-1 and (-)-1 with that of natural akaterpin.
Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Noda, Chiba 278- 8510, Japan.
Hayato
H
Hosoi
Nobuyuki
N
Kawai
Hideki
H
Hagiwara
Takahiro
T
Suzuki
Atsuo
A
Nakazaki
Ken-Ichi
K
Takao
Kazuo
K
Umezawa
Susumu
S
Kobayashi
D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D008968:Molecular Conformation; D054801:Phosphoinositide Phospholipase C / Q000037:antagonists & inhibitors / Q000378:metabolism; D013237:Stereoisomerism; D014315:Triterpenes / Q000138:chemical synthesis / Q000737:chemistry*
D004791:Enzyme Inhibitors; D007659:Ketones; D014315:Triterpenes; C571693:akaterpin; D054801:Phosphoinositide Phospholipase C