Tetrahedron: Asymmetry

Synthesis of (+)-2, 8-dihydroxyethyl-1, 4, 7, 10-tetraoxaspiro [5.5] undecane from (R)-4-hydroxymethyl-2, 2-dimethyl-1, 3-dioxane

S Sauret-Cladière, G Jeminet

Index: Sauret-Cladiere, Sandrine; Jeminet, Georges Tetrahedron Asymmetry, 1997 , vol. 8, # 3 p. 417 - 423

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Citation Number: 4

Abstract

In work on the design of hydrophilic models of calcimycin (or A.23187) (Scheme 1), a calcium ionophore widely used as a biochemical tool 1, we reported a straightforward route to the 2,8- functionalized (+)-E,E-spirobidioxane skeleton 2. For the model with RI =R2=H, to reduce the number of steps in the synthesis, one approach is via the symmetrical spiroacetal bearing CH2-CH2OH arms, which can subsequently be added to. This paper describes the ...