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Home    Συνθετικές προσεγγίσεις στα δριμανικα σεσκιτερπενια. Ανάπτυξη κοινήε συνθετικής μεθοδολογίας στη σύνθεση των cis ΚΑΙ trans 1,1,4a,6-τετραμέθυλο-5-μεθυλενο-1,2,3,4,4a,5,8,8a-οκταϋδροναφθαλενίων  

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Identifier uch.chemistry.msc//2002hatzellis
Title Συνθετικές προσεγγίσεις στα δριμανικα σεσκιτερπενια. Ανάπτυξη κοινήε συνθετικής μεθοδολογίας στη σύνθεση των cis ΚΑΙ trans 1,1,4a,6-τετραμέθυλο-5-μεθυλενο-1,2,3,4,4a,5,8,8a-οκταϋδροναφθαλενίων
Alternative Title Synthetic Approaches towards the Drimane Sesquiterpenes cis- and trans-1,1,4α,6-tetramethyl-5-methylene-1,2,3,4,4α,5,8,8α-octahydronaphthalenes
Creator Hatzellis, Konstantinos
Abstract Labdanum (Cistus creticus, ssp creticus L., Greuter et Burdet) is a perennial shrub that grows in the Mediterranean area, especially in Crete. During the hot summer days its leaves secrete a thick, aromatic resin, called by the locals “ladano”. One of the components isolated from the essential oil of the resin was assigned the structure of a drimane type sesquiterpene namely 1,1,4a,6-tetramethyl-5-methylene-1,2,3,4,4a,5,8,8a-octahydro-napthalene (figure 1). Given that the stereochemistry of the fusion of the decalin ring had not been specified, the aims of the present project were twofold: a) The design of a flexible synthetic pathway towards the target molecules, which upon simple synthetic deviations would lead to both cis / trans isomers. b) The total synthesis of both targets and the comparison of their spectral profiles with those of the natural product. During this project the first target was attained and the second one was realized to the point of total synthesis of the cis isomer in 85% purity. Comparison of spectroscopic data of the synthesized cis-isomer with those from the literature on the trans analog as well as the natural product, indicates that the latter has a different structure than either the cis or trans isomers.
Issue date 2002-07-01
Date available 2002-11-28
Collection   School/Department--School of Sciences and Engineering--Department of Chemistry--Post-graduate theses
  Type of Work--Post-graduate theses
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