Volume 17, Issue 44
Natural Products
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ChemInform Abstract: Cyclic Peptides. Part 22. Synthesis of [2-Amino-2,3-dehydrobutanoic Acid4]AM-Toxin I.

First published: November 4, 1986

Abstract

The coupling reaction of (I) with either (IIa) or (IIb) to give the corresponding products (III), followed by treatment with (IV), yields the open-chain intermediates (V), whose ring Closure provides the Cyclic peptides (VI).

ChemInform Abstract

The coupling reaction of (I) with either (IIa) or (IIb) to give the corresponding products (III), followed by treatment with (IV), yields the open-chain intermediates (V), whose ring Closure provides the Cyclic peptides (VI). Dehydration, preceded by removal of the benzyl group in the case of (VIb), affords the title compound (VIIIa). This analogue of AM-toxinl (VIIIb) displays no toxic activity, indicating the crucial importance of the bulkiness of the dehydroamino acid moiety.

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