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Asymmetric synthesis using chiral acetals highly stereoselective reduction of chiral alpha keto beta gamma unsaturated acetals and its application for the syntheses of r levo and s dextro 3' methoxy 4' o methyljoubertiamine



Asymmetric synthesis using chiral acetals highly stereoselective reduction of chiral alpha keto beta gamma unsaturated acetals and its application for the syntheses of r levo and s dextro 3' methoxy 4' o methyljoubertiamine



Chemical and Pharmaceutical Bulletin 37(8): 2047-2052



Reduction of the chiral .alpha.-keto-.beta.,.gamma.-unsaturated acetals (1) derived from (-)-(2S,3S)-1,4-dimethoxy-2,3-butanediol was studied. Extremely high stereoselectivity was attained with LiAlH4 and two epimeric allyl alcohols (2aA-2cA and 2a.beta.-2cB) were prepared selectively by a proper choice of additive. As an application of this methodology, total syntheses of (R)-(-)-3'-methoxy-4'-O-methyljoubertiamine [(R)-(-)-4] and its enantiomer [(S)-(+)-4] were achieved from the single chiral enone acetal (3) through a highly stereocontrolled reduction followed by the Claisen-Eschenomoser rearrangement.

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Asymmetric synthesis using chiral acetals: Highly stereoselective reduction of chiral .ALPHA.-keto-.BETA.,.GAMMA.-unsaturated acetals and its application for the synthese of (R)-(-)- and (S)-(+)-3'-methoxy-4'-O-methyljoubertiamine. Chemical & Pharmaceutical Bulletin 37(8): 2047-2052, 1989

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