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Stereoselective synthesis of -lactams and carpanone derivatives : dottorato di ricerca in chimica industriale

Fontana, Francesco <1980- >

Tesi o dissertazioni - 2008

SECTION A We here describe the synthesis of new 4-spiro-beta-lactams by means of a Staudinger reaction between ketenes deriving from cyclic, enantiopure alfa-amino acids (protected derivatives of 1,3-thiazolidine-2-carboxylic acid and 4-hydroxy-L-proline) and suitable electron-rich imines. The reactivity of the synthesized compounds has been also evaluated, furnishing totally new and interesting mono- or polycyclic beta-lactams. SECTION B Carpanone is a non optically active lignan incorporating five contiguous stereogenic centers, found in the bark of Carpano Tree. Actually, only one synthetic strategy (limited concerning molecular diversity) for the production of this molecule has been described. We have tuned a new and straightforward (“Diversity Oriented Synthesis”-consistent) synthetic strategy toward carpanone, based on a totally new retrosynthetic analysis. This allowed to convert sesamol into carpanone in six steps with a 55% global yield. Francesco Fontana PhD thesis abstract
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D. 2009 0087
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