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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 23, Number 1
BKCSDE 23(1)
January 20, 2002 

 
Title
An Efficient Synthesis of 12-epi-Carbacyclins Using a Palladium-Mediated Tandem Alkene Insertion Strategy
Author
Nam Ho Lee, Richard C. Larock
Keywords
Prostacyclin, Carbacyclin, Palladium, Organic synthesis, Alkene insertion.
Abstract
A short synthesis of novel prostanoids, 12-epi-carbacyclins 3 and 24, has been accomplished using palladium chemistry as a key step. The silyl enol ether 10a prepared through organopalladium chemistry has been allowed to react with 1-octen-3-one in the presence of Pd(OAc)2 to give compound 12 in a single step. The unusual chemo- and stereoselective reduction of the α,β-unsaturated ketone in 12 has been effected with (S)-BINAL-H. Subsequent desilylation and Wittig reaction have provided the PGI2 analogues 3 and 24.
Page
86 - 92
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