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Total Synthesis of 8-epi-PGF2.alpha.. A Novel Strategy for the Synthesis of Isoprostanes

✍ Scribed by Hwang, Seong Woo; Adiyaman, Mustafa; Khanapure, Subhash; Schio, Laurent; Rokach, Joshua

Book ID: 111685091
Publisher: American Chemical Society
Year: 1994
Tongue: English
Weight: 284 KB
Volume: 116
Category: Article
ISSN: 0002-7863
DOI: 10.1021/ja00102a076

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The first total synthesis of ent-15(RS)-2,3-dinor-5,6-dihydro-8-epi-PGF2c~ 1 is described using diacetone-D-glucose as starting material. The major urinary metabolite of the isoprostane 8-epi-PGF2ct is 2,3-dinor-5,6-dihydro-8-epi-PGF2c~, which is a potent lipid peroxidation index to obtain an integr

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## Smmary: A facile 1,5-migration of a t-butyldimethylsilyl group and a new cleavage reaction of t-butyldimethylsilyl ether to alcohol in prostaglandin intermediates are described.

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The first total synthesis of 15(RS)-5,6-dehydro-8-epi-PGF2cL methyl ester 1 with high stereoselectivity and good yield, is described using D-glucose as starting material. This novel isoprostane is a potent precursor of labelled (deutered and/or tritiated) 8-epi-PGF2a, an useful tool for biological s