Formal synthesis of D-myo-inositol 1, 4, 5-tris (dihydrogen phosphate): cyclization by an unusual ene reaction and use of the Bu2SnCl2/Bu2SnH2 reagent for …

…, X He, MHD Postema, MJ Mashimbye

Index: Clive, Derrick L. J.; He, Xiao; Postema, Maarten H. D.; Mashimbye, M. Jeffrey Journal of Organic Chemistry, 1999 , vol. 64, # 12 p. 4397 - 4410

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Citation Number: 30

Abstract

d-Glucose was converted into the propargyl silane aldehyde 5, which, on treatment with camphorsulfonic acid, cyclized with retention of silicon. The allenic product (7) was elaborated via ketone 24 into 4, which had previously been converted into d-myo-inositol 1, 4, 5-tris (dihydrogen phosphate). Selective reduction of the advanced intermediate 24 was accomplished with Bu2SnCl2/Bu2SnH2, a reagent mixture that shows a very strong ...