A short formal synthesis of squalamine from a microbial metabolite.
A short formal synthesis of squalamine is described, utilizing the biotransformation product 2, which is available in one step from commercially available 3-keto-23,24-bisnorchol-4-en-22-ol (1). Regioselective C-22 oxidation and C-24 sulfation of the corresponding alcohols in the presence of a free C-7 alcohol make for an efficient preparation of squalamine intermediate 11.
Kinney
W A
WA
Magainin Pharmaceuticals Inc., 5110 Campus Drive, Plymouth Meeting, Pennsylvania 19462, USA. wkinney1@prius.jnj.com
Zhang
X
X
Williams
J I
JI
Johnston
S
S
Michalak
R S
RS
Deshpande
M
M
Dostal
L
L
Rosazza
J P
JP
D020533:Angiogenesis Inhibitors / Q000138:chemical synthesis*; D002777:Cholestanols / Q000138:chemical synthesis*; D006900:Hydroxylation; D003904:Mitosporic Fungi / Q000378:metabolism; D009654:Norsteroids / Q000737:chemistry / Q000378:metabolism
C414922:3-keto-23,24-bisnorchol-4-en-22-ol; D020533:Angiogenesis Inhibitors; D002777:Cholestanols; D009654:Norsteroids; C079655:squalamine