Eleven members of the homologous series of paradols, of which one, [6] paradol (n-heptyl 4-hydroxy-3-rnethoxyphenethyl ketone), occurs naturally in the seeds of Amomum melegueta Roscoe (Zingiberaceae) (otherwise known as Grains of Paradise, Guinea pepper, or Melegueta pepper), have been synthesised by an improved method. Physical characteristics, including g.1.c. behaviour, and pungency evaluation experiments are described for the series.THE paradols 1 ~2 are a series of phenolic ketones of general formula (1), structurally related to the gingerols (2) and the shogaols (6).3 Representatives of all three types of molecule have been identified l s 3 as pungent principles in the oleoresin of commercial extracts of ginger, prepared from the rhizomes of the tropical plant Ziizgiber oflcinale Roscoe (Zingiberaceae) ; [6]gingerol (3) and [6]paradol (13) have been found in the seeds of Amomum melegueta Roscoe (Zingiberaceae) , variously known as Grains of Paradise, Guinea pepper, or Melegueta pepper .4t The number bracketed before the name designates the number of carbon atoms in the aldehyde which would be produced by a retro-aldol reaction on the gingerol (2). Thus each gingerol (2) is identified by the length of this potentially aldehydic portion of the side chain. To ensure consistency, the same nomenclature has been adopted to cover the shogaols (6) and the paradols ( l ) , though it is recognised that the latter cannot undergo retro-aldol fission.$ B. P. Appl. 45379/1972.
Prostaglandin-Fza has been synthesised from cyclopentadiene in a highly stereoselective ten-step sequence of reactions. The key step involves the coupling of a protected 3-hydroxyoct-1 -enyl unit to 3-dimethyl-t-butylsilyloxytricyclo [3.2.0.02*'] heptan-6-one through the use of a mixed organocuprate reagent.We are grateful to the S.R.C. and Allen and Hanburys Research for financial support (C.A.S.E. award to T. V. L.). Our thanks are due to Mr. John Paton for technical assistance.
Über das gespannte Cyclopropylketon (IV), das aus dem Bromhydrin (III) durch Behandlung mit Dimethyl‐tert.‐butylsilylchlorid/Imidazol in Dimethylformamid und anschließende Dehydrobromierung mit Kalium‐tert.‐butylat zugänglich ist, wird das gesuchte Prostaglandin (IX) dargestellt.
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