Synthesis of d- and l-isoiridomyrmecin and related compounds
1959; Elsevier BV; Volume: 6; Issue: 3 Linguagem: Inglês
10.1016/0040-4020(59)80003-x
ISSN1464-5416
AutoresKyle J. Clark, G. I. Fray, R.H. Jaeger, Robert Robinson,
Tópico(s)Microbial Natural Products and Biosynthesis
ResumoStaring from d-citronellal of natural origin, d-iridodial and d-isoiridomyrmecin were synthesised.1 The latter furnished, on oxidation, a nepetalinic acid, which was the enantiomorph of a degradation product of nepetalactone. A mixture of the two specimens afforded a racemate of higher melting point. l-Citronellal, obtained (Boake, Roberts & Co.) by a series of chemical transformations from pinene was similarly converted into l-iridodial and l-isoiridomyrmecin. The latter was identical with the natural product from Iridomyrmex nitidus.
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