Synthesis of the shark repellent pavoninin-4.
[reaction: see text] The first synthesis of the shark repellent pavoninin-4, 3, was achieved in 12 steps with 21% overall yield from diosgenin, 8. Key reactions involve an efficient synthesis of the C-15alpha hydroxyl steroid from a C-16beta hydroxyl steroid by an unexpected 1,2-transposition strategy, a stereospecific glycosylation of a hindered C-15alpha alcohol using glycosyl fluoride as a glycosyl donor and a highly chemoselective acetylation of the C-26 primary alcohol by catalytic transesterification.
Williams
John R
JR
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122-2585, USA. john.r.williams@temple.edu
Gong
Hua
H
Hoff
Nathan
N
Olubodun
Olaoluwa I
OI
D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D002784:Cholesterol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D012754:Sharks
D000617:Aminoglycosides; D002784:Cholesterol; C507447:pavoninin-4