36183-27-4Relevant academic research and scientific papers
Stereoselective Synthesis of Alcohols, XII. Synthesis of the C-9/C-13 Partial Structure of Methynolide
Hoffmann, Reinhard W.,Ladner, Wolfgang
, p. 1631 - 1642 (2007/10/02)
Reduction of the β-ketoester 5 by yeast led to the β-hydroxyester 7, which was converted to the epoxyesters 13 and 15.Their transformation into the dioxolane carboxylic esters 14 and 16 by SnCl4/acetone proceeded under inversion at C-3.The structure 14 was secured by independent synthesis from D-ribonolactone.The enolate derived from 14 or 16 gave on methylation predominantly the cis-substituted product 21.The isomeric product 2 was obtained from D-fructose in six steps.
