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Synthesis and investigation of the optically active compounds from α-pinene


Author: Gudima Alexandru
Degree:doctor of chemistry
Speciality: 02.00.03 - Organic chemistry
Year:2009
Scientific adviser: Fliur Macaev
doctor habilitat, professor, Institute of Chemistry, Academy of Sciences of Moldova
Institution:
Scientific council:

Status

The thesis was presented on the 6 November, 2008
Approved by NCAA on the 22 January, 2009

Abstract

Adobe PDF document0.37 Mb / in romanian
Adobe PDF document0.42 Mb / in russian

Thesis

CZU 547.598.05(043.3)+547.94.05(043.3)

Adobe PDF document 0.91 Mb / in russian
106 pages


Keywords

monoterpenoids, sesquiterpenoids, alkaloids, oxindoles, chiral lactames, ionic liquids, electrochemical oxidation, ozonolysis.

Summary

The thesis is dedicated to the elaboration of new selective methods of synthesis of the optically active compounds from accessible monoterpene α-pinene.

The syntheses of the natural antifidant cryptomerlone and monoterpene carvone were elaborated for the first time. It has been found that effective method for the preparation of common precursor of above compounds is electrochemical anode oxidation of α-pinene.

Simple method for the preparation of analogs of natural alkaloids based on synthesized 1,3-disubstituted 2,2-dimethylcyclobutanes and isatines it was developed.

Ozone oxidation of α-pinenes in the mixture of CH2Cl2/Py was proposed as a technological scheme for the synthesis of chiral cyclobutanes - important synthons for the preparation of biologically active compounds. The structure of obtained products depends on temperature of reaction as well as of quantity of ozone. The reaction conditions make possible selective preparation of the target 1,3-substituted 2,2-dimethylcyclobutanes.

The influence of a nature of catalysts on regio- and chemoselectivity reactions of synthesis of derivates of pinonic acid is revealed.

At the first time the synthesis of chiral lactam-based ionic liquids was carried out by the use of the products of cycloaddition reaction of chlorosulfonylisocyanate to enantiomeric α-pinenes.

A number of heterocyclic derivatives of 2,2-dimethylcyclobutane, some of which possess the potential anti-HIV-1 activity was synthesized.

The results of this investigation has not only academic, but also have importance practical interest due to discovered of new synthetic pathways for the preparation of such practically important natural compounds, as cryptomerlone, carvone and synthetic analogs of marine alkaloids.