Lilac alcohols

Treatment of the selenide (19) with unbuffered 30% hydrogen peroxide-THF yields the cis- and trans-linalyl oxides (247) via [2,3] sigmatropic rearrangement. Kossanyi et al. have improved upon the efficiency of Vig s synthesis of the four lilac alcohols (248). The synthesis of the furanoid (249), formed during sulphuric acid-catalysed dimerization of isoprene, is straightforward. The known half-... 

Nonactic Acid, Lilac Alcohol and Prelog-Djerassi Lactone... 

The cycloadduct (75d) has been utilized for the synthesis of nonactic acid (116) and lilac alcohol (119) via (118). The Prelog-Djerassi lactone (117), a pivotal intermediate in Masamune s methymycin synthesis, has been prepared tom the key compound (75e) (Scheme 21)J ... 

Two isomers of linalool oxide have been isolated from lilac Syringa vulgaris L.) flower oil, " and their syntheses from ( + )-linalyl acetate have been effected following Scheme 19 the four diastereoisomers of the lilac alcohols (323) were separated by gas chromatography.It should be added that the aldehydes in this series were prepared elsewhere by direct cyclization with sodium carbonate in methanol of the selenium oxide oxidation product of linalyl acetate. " ... 

There are many compounds closely related to natural products that are associated with novel syntheses. Dehydrated linalool oxide 891, for example, is conveniently made by chlorination of linalool acetate (28 acetate) with calcium hypochlorite, then cyclization of the allyl chloride 892 with sodium hydroxide and Aliquat 336 in methanol. Once obtained 891 was converted to the dehydrogenated lilac alcohols 893 (R = H). The monoepoxides (on the isopropenyl group) were transformed in a mixture of diacetates that were pyrolyzed to the acetates 893 (R = Ac). Linalool oxide epoxides (894) have... 

A ketol ether (410) which, so far as the Reporter knows, is a new natural product, has been isolated from Perilla frutescens var. acuta. All four of the lilac alcohol (411) isomers are present in the oil from flowers of lilac, a complete analysis of which has been published. Further work on the irradiation of -carotene [yielding loliolide (412), Vol. l,p. 50] has revealed the presence of further products the same reaction with zeaxanthin (413) yields the same substances, with, in addition, 3-hydroxy-/ -cyclocitral (414). ... 

Wakayama, S., S. Namba, and M. Ohno Lilac Alcohol-a and -b. New Naturally Occurring Odor Ingredients. Bull. Chem. Soc. Japan 43, 3319 (1970) Chem. Abstr. 74, 91089c (1971). 

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