Diastereomers of 3-amino-2-hydroxy-6-methylheptanoic acid (AHMHA), a new amino acid unit in perthamides C and D, have been synthesized from commercially available 4-methylpentanol in a concise manner and 50% average overall yield. Comparison of the 1H and 13C NMR data, optical rotation data and Marfey’s analysis of the resulting isomers with the natural fragment unambiguously allowed the configurational assignment of the natural residue as (2R,3R). A structural revision of perthamides C and D is also reported.
Concise synthesis of AHMHA unit in perthamide C. Structural and stereochemical revision of perthamide C / Sepe, Valentina; D'Auria, MARIA VALERIA; Bifulco, G.; Ummarino, Raffaella; Zampella, Angela. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 66:38(2010), pp. 7520-7526. [10.1016/j.tet.2010.07.060]
Concise synthesis of AHMHA unit in perthamide C. Structural and stereochemical revision of perthamide C
SEPE, VALENTINA;D'AURIA, MARIA VALERIA;UMMARINO, RAFFAELLA;ZAMPELLA, ANGELA
2010
Abstract
Diastereomers of 3-amino-2-hydroxy-6-methylheptanoic acid (AHMHA), a new amino acid unit in perthamides C and D, have been synthesized from commercially available 4-methylpentanol in a concise manner and 50% average overall yield. Comparison of the 1H and 13C NMR data, optical rotation data and Marfey’s analysis of the resulting isomers with the natural fragment unambiguously allowed the configurational assignment of the natural residue as (2R,3R). A structural revision of perthamides C and D is also reported.| File | Dimensione | Formato | |
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