An efficient and highly stereocontrolled synthesis of (2R,3R,4R,6R)-3-hydroxy-2,4,6-trimethyloctanoic acid, the beta-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% overall yield. Comparison of the 1H and 13C NMR and optical rotation data of the resulting beta-hydroxy acid with the natural fragment unambiguously verifies the configurational assignment as (2R,3R,4R,6R).
Synthetic studies on homophymine A: stereoselective synthesis of (2R,3R,4R,6R)-3-hydroxy-2,4,6-trimethyloctanoic acid / F., Bellotta; D'Auria, MARIA VALERIA; Sepe, Valentina; Zampella, Angela. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 65:18(2009), pp. 3659-3663. [10.1016/j.tet.2009.02.069]
Synthetic studies on homophymine A: stereoselective synthesis of (2R,3R,4R,6R)-3-hydroxy-2,4,6-trimethyloctanoic acid
D'AURIA, MARIA VALERIA;SEPE, VALENTINA;ZAMPELLA, ANGELA
2009
Abstract
An efficient and highly stereocontrolled synthesis of (2R,3R,4R,6R)-3-hydroxy-2,4,6-trimethyloctanoic acid, the beta-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% overall yield. Comparison of the 1H and 13C NMR and optical rotation data of the resulting beta-hydroxy acid with the natural fragment unambiguously verifies the configurational assignment as (2R,3R,4R,6R).I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
