Liebigs Annalen

Enantioselective synthesis of bis (γ??butyrolactones). Their oxidative degradation to tetraols as a key step in stereoselective syntheses of 1, 3, 5, 7, 9??pentaol synthons …

M Menges, R Brückner

Index: Menges, Markus; Brueckner, Reinhard Liebigs Annalen, 1995 , # 2 p. 365 - 384

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Citation Number: 6

Abstract

Abstract The syntheses of two enantiopure skipped-chain pentaol building blocks 51 and 56 are described. They are based on a strategy which derives 1, 3, 7, 9-tetraols from bis (γ- butyrolactones). Two equivalents of γ-lactone 17, readily available from L-glutamic acid, and one equivalent of the diiodoisobutene 22 furnished bis (γ-butyrolactone) trans, trans-21 stereoselectively in a single step. The same lactone, combined in a 2: 1 ratio with the ...