Stereoselective and Efficient Synthesis of (3 R, 3a S, 6a R)-Hexahydrofuro [2, 3-b] furan-3-ol

…, BRR Kesteleyn, PBTP Wigerinck, NMF Goyvaerts…

Index: Quaedflieg, Peter J. L. M.; Kesteleyn, Bart R. R.; Wigerinck, Piet B. T. P.; Goyvaerts, Nicolaas M. F.; Vijn, Robert Jan; Liebregts, Constantinus S. M.; Kooistra, Jaap H. M. H.; Cusan, Claudia Organic Letters, 2005 , vol. 7, # 26 p. 5917 - 5920

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Citation Number: 33

Abstract

Two short and efficient synthesis routes have been developed for bis-THF-alcohol 2, a key building block of the investigational HIV protease inhibitor TMC114 (1). Using S-2, 3-O- isopropylideneglyceraldehyde (4) as the source of chirality, both routes are based on a diastereoselective Michael addition of nitromethane to give predominantly the syn congeners 6 followed by a Nef oxidation and cyclization to afford lactone acetals 8, which ...