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03/01/2012 · Biosynthesis of Linalool

(–)-TTC was used in the total synthesis of (+)-linalool oxide (1.247) which was achieved in 9 steps and 13% overall yield.

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A new synthesis of (±) linalool - ScienceDirect

Most natural materials contain (almost) exclusively one enantiomer, but laboratory synthesis generally gives a mixture. Genuine lavender oil is at least 85% () –enantiomer; likewise the ()-isomer of linalool predominates (94-96%) in authentic sweet orange oil. So determination of enantiomeric composition can provide a test for any adulteration and of the authenticity of the oil.

Enantioselective synthesis of each stereoisomer of the pyranoid linalool oxides: the linalool route

Plants, though, don’t make it by joining isoprenes together. As so often, biosynthesis starts with acetyl coenzyme A, which undergoes a series of enzyme-controlled reactions to generate mevalonic acid; this in turn affords isopentenyl pyrophosphate (IPP), whose more stable isomer dimethylallyl pyrophosphate (DMAPP) is a source of a carbocation which reacts with an IPP forming geranyl pyrophosphate. These reactions are controlled by monoterpene synthase enzymes, and it is one of these, linalool synthase, that is responsible for the formation of linalool.

English: Chemical synthesis of linalool from alpha-pinene

Synthesis of (+)-Linalool Oxide Derivatives of the …

A classic synthesis employed by Ruzicka and Fornasir used nucleophilic attack of the acetylide ion upon methyl heptenone to afford dehydrolinalool. Selective reduction of the alkyne linkage with sodium gave linalool.

The thermal decomposition of linalool oxide fueanoid 1 and linalool oxide furanoid acetate 2 in the presence of synthetic zeolites (3 A, 4 A, 5 A, and 13 X) was investigated. With zeolite 3 A at 300°C, karahanaenone 5 was synthesized with selectivity (highest yield obtained, 61%) from 2. Five alcohols were synthesized by the Grignard reaction from ketone 5 with C1_??_C4 alkyl bromides. Acetylation of these alcohols by treatment with acetic anhydride gave the corresponding acetate derivatives. The odor of these compounds was evaluated, methyl, ethyl, and propyl alcohol derivatives had odors that would qualify them for use as flavor materials.

Chemical synthesis of linalool from acetone and acetylene

30/05/2007 · Research Article Direct Synthesis of Linalyl Acetate from Linalool in Supercritical Carbon Dioxide: A Thermodynamic Study

01/06/2010 · A new cyclohexyl-based chiral auxiliary: application in the total synthesis of (+)-linalool oxide
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