Synthetic studies on homophymine A: Stereoselective synthesis of (2R, 3R, 4R, 6R)-3-hydroxy-2, 4, 6-trimethyloctanoic acid

F Bellotta, MV D'Auria, V Sepe, A Zampella

Index: Bellotta, Filomena; D'Auria, Maria Valeria; Sepe, Valentina; Zampella, Angela Tetrahedron, 2009 , vol. 65, # 18 p. 3659 - 3663

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Citation Number: 4

Abstract

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 ...