Converting a Birch Reduction Product into a Polyketide: Application to the Synthesis of a C1–C11 Building Block of Rimocidin
L Nachbauer, R Brückner
Index: Nachbauer, Luc; Brueckner, Reinhard European Journal of Organic Chemistry, 2012 , # 35 p. 6904 - 6923
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Abstract
Abstract A stereoselective synthesis of a C 1–C 11 building block for the polyol-polyene antibiotic rimocidin has been developed. Its functional groups originate from a disubstituted indane, which underwent Birch reduction, and oxidative cleavage. This provided a dihydropyranone with a β-keto ester side-chain. The latter was subjected to a Noyori hydrogenation (ds> 97: 3). An oxy-Michael addition gave a mixture of two spiroketals. ...
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