Synthetic studies on homophymine A: stereoselective synthesis of (2R

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• 作者：Filomena Bellotta ; Maria Valeria D'Auria ; Valentina Sepe ; Angela Zampella
• 刊名：Tetrahedron
• 出版年：2009
• 出版时间：2 May 2009
• 年：2009
• 卷：65
• 期：18
• 页码：3659-3663
• 全文大小：215 K

文摘

An efficient and highly stereocontrolled synthesis of (2R,3R,4R,6R)-3-hydroxy-2,4,6-trimethyloctanoic acid, the β-hydroxy acid unit that acylates the N-terminus of homophymine A, has been devised starting from iodoethane and (S,S)-pseudoephedrine propionamide in 9 steps and 36 % average overall yield. Comparison of the ¹H and ¹³C NMR and optical rotation data of the resulting β-hydroxy acid with the natural fragment unambiguously verifies the configurational assignment as (2R,3R,4R,6R).