Document Report Card

ID: ALA1158092

Journal: J Nat Prod

Title: Discovery, synthesis, and insecticidal activity of cycloaspeptide E.

Authors: Lewer P, Graupner PR, Hahn DR, Karr LL, Duebelbeis DO, Lira JM, Anzeveno PB, Fields SC, Gilbert JR, Pearce C.

Abstract: Several Penicillia and one Tricothecium strain produced a new, insecticidally active member of the cycloaspeptide family, with the proposed name cycloaspeptide E (1). The structure, which was determined on the basis of spectroscopic (NMR, UV, MS) data and Marfey amino acid analysis, was the tyrosine desoxy version of cycloaspeptide A (2). Two synthetic routes to compound 1 were developed: one a partial synthesis from 2 and the other a total synthesis from methyl alaninate hydrochloride. Cycloaspeptide E, the first member of this series not to contain a tyrosine moiety, is also the first to be reported with insecticidal activity.

CiteXplore: 17067173

DOI: 10.1021/np060219c