Formal synthesis of squalamine from desmosterol.
The key intermediate to squalamine, (5alpha,7alpha,24R)-7,24-dihydroxy-cholestan-3-one, was synthesized from the 3-O-acetyl-24R,25-dihydroxy derivative of desmosterol via 10 steps in 16% overall yield and squalamine was also prepared via two further steps in 7.4% total yield from the desmosterol derivative.
Okumura
Kazuo
K
Niigata University of Pharmacy and Applied Life Sciences, Japan.
Nakamura
Yutaka
Y
Takeuchi
Seiji
S
Kato
Isao
I
Fujimoto
Yoshinori
Y
Ikekawa
Nobuo
N
D002777:Cholestanols / Q000138:chemical synthesis* / Q000378:metabolism; D003897:Desmosterol / Q000737:chemistry* / Q000378:metabolism
D002777:Cholestanols; D003897:Desmosterol; C079655:squalamine