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Enantiodivergent Formal Total Synthesis of Aspercyclide C from L-(+)-Tartaric Acid

  作者 PRASAD KAVIRAYANI R; GANDI VASUDEVA RAO; NIDHIRY JOHN EUGENE; BHAT KAVYA S  
  选自 期刊  Synthesis;  卷期  2010年-15;  页码  2521-2526  
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[摘要]The enantiodivergent formal syntheses of both enantiomers of aspercyclide C is accomplished. Starting from L-(+)-tartaric acid, the key protected allylic alcohol, (3R,4R)-4-(methoxy-methoxy) non-1-en-3-ol is prepared, and is then elaborated into both enantiomers of 3-[(4-methoxybenzyl)oxy]non-1-en-4-ol via Mitsunobu inversion. Esterification with a known biaryl acid, followed by ring-closing metathesis and deprotection completes the syntheses.

 
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