Presented as Thesis (Ph. D.)--University of Wisconsin--Madison, 1916. / Reprinted from Journal of the American Chemical Society, vol. XXXIX, no. 3 (Mar. 1917). Includes bibliographical references.

L’ionomycine est un ionophore produit par la bactérie gram-positive streptomyces conglobatus. Sa synthèse représente un défi, car il possède plusieurs centres chiraux dans un motif polypropylène. De plus, la grande densité d’oxygène sur celui-ci oblige l’utilisation de plusieurs protections orthogonales. Notre stratégie divise l’ionomycine en quatre fragments, trois possédant le motif polypropylène, ainsi qu’un quatrième, bis-tétrahydrofuranne. Les trois premiers sont synthétisés en utilisant une méthodologie puissante développée dans le laboratoire du Pr Spino, qui utilise l’addition d’alkylcyanocuprates sur les carbonates allyliques dérivés de la menthone. Celle-ci permet l’introduction d’une unité propylène, avec un excellent contrôle du centre chiral introduit. Cette méthode est utilisée de manière itérative, afin d’introduire plusieurs unités propylènes. De plus, notre stratégie est hautement convergente, puisque des intermédiaires des fragments plus courts servent de produit de départ pour la synthèse des fragments plus longs. Le dernier fragment, bis-tétrahydrofuranne, a été fabriqué à partir de l’acétate de géranyle, par une polycyclisation d’un diépoxyde chiral, les époxydes ayant été introduits par une époxydation de Shi. Cette synthèse, si complétée, serait la plus courte publiée, avec 24 étapes pour la séquence linéaire la plus longue (51 au total).

Abstract Peppermint (Mentha x piperita L.) oil is one of the most popular and widely used essential oils, mostly because of its main components menthol and menthone. Peppermint oil is used for flavouring pharmaceuticals and oral preparations. Corn mint is the richest source of natural menthol. Carvone-scented mint plants, such as spearmint (M. spicata), are rich in carvone and are widely used as spices, and they are cultivated in several countries. Studies were made into the yield and essential oil content of several mint species and the original. The general aim of the work was to examine the optimal conditions for cultivating mint in Northern Finland. The specific aims of the study were (first) to investigate the differences in the oil content for several mint species and (secondly) to compare the effect of various factors such as plant spacing (10, 20 and 30 × 50 cm), liming (0, 4, 8, 12 and 16 tons ha-1), propagation methods (micropropagated and conventionally propagated plants) and harvest date (once at the end of August in comparison with first cut at the beginning of August and second cut in mid September) on the cultivation success, quality and quantity of the plants. The constituents of the essential oil were analysed from leaf samples using GC-MS. Among the peppermints of different origins studied, peppermint of USA and Egypt origin ('Black Mitcham') contain the highest menthol and optimum oil yield. Corn mint and Sachalin mints both had high menthol content. Due to several reasons, such as no significant differences between the different densities and oil composition, markedly higher amount of weeds at 30 × 50 cm than at 10 × 50 and 20 × 50 cm spacing and the high seedling costs and the danger of fungi and disease at a 10 × 50 cm spacing, a plant optimum of 20 × 50 cm spacing is recommended for Northern Ostrobothnia. If the pH value is lower than 6, or levels of Mg and Ca are low, liming at a rate of 4–8 t ha-1 for sandy soils in Finland is recommended in order to achieve higher fresh and oil yields. In the first year, there were no differences in the dry leaf yield of micropropagated and conventionally propagated plants, but the menthol content was significantly higher in conventionally than in micropropagated plants. In the second year, only the dry leaf yield of micropropagated plants was higher than that of their conventionally propagated counterparts. Cutting peppermint only once during full bloom (the end of August) gives the maximum oil yield of good quality. In conclusion, it is possible to achieve as high as or even higher oil quality and dry yield in North Ostrobothnia than it is in central Europe or south Asia. However, this requires observing certain cultivation factors such as having the right type of mint, soil pH, planting density, harvesting time and propagation method In addition, mints must be cultivated in the same place for only two and a maximum for three years.