Journal of Organic Chemistry p. 3853 - 3857 (1990)
Update date:2022-07-30
Topics:
Barrett, Anthony G. M.
Lebold, Suzanne A.
The stereospecific total synthesis of polyoxin C and the nucleoside analogue, uracil polyoxin C, is described.Condensation of (phenylthio)nitromethane with methyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside 5 gave the (Z)-nitro olefin 6.Addition of potassium trimethylsilanoate and ozonolysis gave the α-hydroxy thioester 7, which was formed with excellent diastereoselectivity.The alcohol 7 was converted into polyoxin C (1) and uracil polyoxin C (2) via the azide 11 and base incorporation using the Vorbrueggen method.
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