A bacterium having close affinity with Pseudomonas flava was isolated from eucalypt leaves for its ability to utilize 1,8-cineole (1) as a carbon source. The bacterium is also capable of utilizing α-terpineol, camphor, isoborneol and geraniol but failed to grow on borneol, limonene and piperitone. Growth of the organism in mineral salts medium containing 1,8-cineole resulted in the formation of four oxidation products. Keto lactone (2), alcohols (3) and (4) and ketone (5) arereported as natural products arising from the oxidation of 1,8-cineole by the bacterium.

The 13s compound 13-epiisomanool (labda-8,14-dien-138-01) has been synthesized and its optical rotation compared with that of the 13R isomer (isomanool) in order to correct errors in the literature.The 13s compound labda-8,14-dien-13P-01 (1) has been reported1 (" 13-epiisomanool") to be an oil, [a], -I-27.5" ([4], $80). The rotation of this compound, reputedly lower than that of the 13R epimer (2) ("isomanool"), was used erroneously to assign the C 13 stereochemistry to a number of compounds in this series.$ The results have been commented upon.' § During a survey of optical rotation and structure in the labdan~ids,~ we calculated that compound (1) should have a molecular rotation at 589 nm of $260 units, and that it should have a larger positive rotation than epimer (2). Compound (1) is entry 103 in the earlier paper,3 while (2) is entry 102, with the compounds now renamed to meet modern nomenclature requirement^.^The discrepancy between observed and calculated rotations for (1) was so great that it was considered3 that either the compound did not have the assigned structure or else its optical rotation had been incorrectly determined.Compound (1) ("isoepimanool") has also been isolated from a natural sources but no rotation was reported.We now record the synthesis of compound (1) from 13-epimanool (3). Isomerization of the 8(17) double bond of (3) under acid conditions is attended with considerable rearrangement of the allylic alcohol, but basic conditions using lithium * Part XXXI, Aust. J. Chem., 1973, 26, 209. t Chemistry Department, University of Queensland, St. Lucia, Qld. 4067.f The workers in reference 1 made two errors which fortuitously compensated. They had the rotations of (1) and (2) in the wrong order, but they took (-)-linalool to be S and it was not until later (Cornforth, R. H., Cornforth, J. W., and Prelog, V., Liebigs Ann., 1960, 634, 197) that (-)-linalool was proved to have the R configuration.$ The Italian workers misapply the R,S nomenclature in some instances.

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I. M. SHAW and A. TAYLOR. Can. J. Chem. 64, 164 (1986).4-Chlorobenzoylazide reacts with amino acid and peptide esters to give the 4-chlorobenzoyl derivatives in 60-90% yield, at room temperature, without measurable racemization. The reaction also proceeds smoothly with hindered amines such as methyl 2-methylalaninate and with secondary amines, e.g. methyl L-prolyl-L-valinate. Ten examples of the reaction are reported with peptides, synthesized for the purpose, that might be accessible from hydrolysates of the numerous fungal metabolites now known, which contain a high proportion of 2-methylalanine. The derivatives of di-, tri-, tetra-, and pentapeptides were highly crystalline, with sharp melting points, and could be detected and integrated in the effluent from chromatography columns at about the 10-ng level. This simple method of derivatization might be usefully applied to the resolution of discrepancies in the physical properties of ostensibly the same 2-methylalanyl peptide prepared in different laboratories.I. M. SHAW et A. TAYLOR. Can. J. Chem. 64, 164 (1986). L'azoture du chloro-4 benzoyle rkagit avec les esters d'acides aminks et de peptides, B la tempCrature ambiante, pour conduire aux dCrivks chloro-4 benzoylks avec des rendements de 60 i i 90% et sans rackmisation mesurable. La rkaction se produit aussi facilement avec des amines encombrkes, comme le mCthyl-2 alaninate de mkthyle, et avec des amines secondaires, comme le L-prolyl-L-valinate de mkthyle. On rapporte dix exemples de la reaction avec des peptides, synthCtisCs B cette fin, qui peuvent se retrouver dans les hydrolysats de plusieurs mktabolites de champignons qui sont maintenant connus pour contenir une grande proportion de mkthyl-2 alanine. Les dkrivCs des di-, tri-, tetra-et pentapeptides sont trks cristallins, ils ont des points de fusion bien dkfinis et ils peuvent itre dCtectks et intCgrCs en chromatographie a des niveaux de 10 ng. Cette simple mCthode de prkparer un dkrivC peut itre appliquke utilement B la rksolution des diffkrences dans les propriktks physiques de peptides de la methyl-2 alanine qui semblent les mimes, mais qui ont Ctk prCparCs dans des laboratoires diffkrents.

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