Prasad, Kavirayani R and Gandi, Vasudeva Rao and Nidhiry, John Eugene and Bhat, Kavya S (2010) Enantiodivergent Formal Total Synthesis of Aspercyclide C from L-(+)-Tartaric Acid. In: Synthesis (15). pp. 2521-2526.
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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.
|Item Type:||Journal Article|
|Additional Information:||Copyright of this article belongs to Thieme Medical Publishers.|
|Keywords:||Aspercyclide C; total synthesis; tartaric acid; Mitsunobu inversion; ring-closing metathesis.|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||26 Oct 2010 06:59|
|Last Modified:||26 Oct 2010 06:59|
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