jo051733a_si_001.pdf (2.74 MB)
Synthesis of the Shark Repellent Pavoninin-4
journal contribution
posted on 2005-12-23, 00:00 authored by John R. Williams, Hua Gong, Nathan Hoff, Olaoluwa I. OlubodunThe 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-15α hydroxyl steroid
from a C-16β hydroxyl steroid by an unexpected 1,2-transposition strategy, a stereospecific
glycosylation of a hindered C-15α alcohol using glycosyl fluoride as a glycosyl donor and a highly
chemoselective acetylation of the C-26 primary alcohol by catalytic transesterification.