Synthesis of the insect feeding deterrent peramine via Michael addition of a pyrrole anion to a nitroalkene
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 2,p. 311-314
- https://doi.org/10.1039/p19900000311
Abstract
A total synthesis of peramine (1), the major insect feeding deterrent isolated from perennial ryegrass (Lolium perenne L.) infected with the endophytic fungus Acremonium lolii is reported. The key step involves the Michael addition of the potassium salt of methyl pyrrole-2-carboxylate (3) to the nitroalkene (4) providing access to a 3-substituted pyrrolo[1,2-a]pyrazin-1 (2H)-one (10). Displacement of the allylic bromide (11) by cyanomethyl cuprate provided the methodology for introducing the desired monosubstituted guanidino group via the nitrite (12).This publication has 3 references indexed in Scilit:
- Total synthesis of peramineThe Journal of Organic Chemistry, 1988
- Synthesis of 2-Methylpyrrolo[1,2-a]pyrazin-1(2h)-oneAustralian Journal of Chemistry, 1988
- Isolation of feeding deterrents against argentine stem weevil from ryegrass infected with the endophyteAcremonium loliaeJournal of Chemical Ecology, 1986