Synthesis of the promising chiral synthon isopropyl-4R-methyl-6-iodohexanoate from L-(-)-menthol

A synthesis of the promising optically pure synthon isopropyl-4R-methyl-6-iodohexanoate based on ozonolytic transformation of the product of regiospecific dehydratation of L-(-)-menthol, (R)-p-menth-3-elle, into 2,6R-dimethyl-8-hydroxyoctan-3-one was proposed.

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Bibliographic Details
Published inChemistry of natural compounds Vol. 41; no. 1; pp. 41 - 44
Main Authors Ishmuratov, GY, Yakovleva, MP, Ganieva, VA, Muslukhov, RR, Tolstikov, GA
Format Journal Article
LanguageEnglish
Published NEW YORK Kluwer Academic/Plenum Publishers 01.01.2005
Subjects
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Physical Sciences
Science & Technology
sodium tris-acetoxyborohydride
ozonolysis
PHEROMONE
(R)-p-menth-3-ene
L-(-)-menthol
3R,7-dimethyloctan-1,6S-diol
REARRANGEMENTS
3R,7-dimethyl-6-oxooctyl ester of 3R,7-dimethyl-6-oxooctanoic acid
2,6R-dimethyl-8-hydroxyoctan-3-one
3R,7-dimethyl-6-oxooctanoic acid
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Summary:A synthesis of the promising optically pure synthon isopropyl-4R-methyl-6-iodohexanoate based on ozonolytic transformation of the product of regiospecific dehydratation of L-(-)-menthol, (R)-p-menth-3-elle, into 2,6R-dimethyl-8-hydroxyoctan-3-one was proposed.
ISSN:0009-3130
1573-8388
DOI:10.1007/s10600-005-0070-6