An Efficient Synthesis of 12-epi-Carbacyclins Using a Palladium-Mediated Tandem Alkene Insertion Strategy 


Vol. 23,  No. 1, pp. 86-92, Jan.  2002
10.5012/bkcs.2002.23.1.086


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  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(OAc2 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 PG2 analogues 3 and 24.

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  Cite this article

[IEEE Style]

N. H. Lee and R. C. Larock, "An Efficient Synthesis of 12-epi-Carbacyclins Using a Palladium-Mediated Tandem Alkene Insertion Strategy," Bulletin of the Korean Chemical Society, vol. 23, no. 1, pp. 86-92, 2002. DOI: 10.5012/bkcs.2002.23.1.086.

[ACM Style]

Nam Ho Lee and Richard C. Larock. 2002. An Efficient Synthesis of 12-epi-Carbacyclins Using a Palladium-Mediated Tandem Alkene Insertion Strategy. Bulletin of the Korean Chemical Society, 23, 1, (2002), 86-92. DOI: 10.5012/bkcs.2002.23.1.086.

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ISSN(Print) 0253-2964
ISSN(Online) 1229-5949