Κατεύθυνση Οργανική Χημεία
Library of the School of Science

2014-12-09

2014

Σύψα Ανθή

Δημήτριος Γεωργιάδης, Επίκουρος Καθηγητής ΕΚΠΑ (Επιβλέπων Καθηγητής), Βικτωρία Μαγκριώτη, Λέκτορας ΕΚΠΑ, Γεώργιος Βουγιουκαλάκης, Λέκτορας ΕΚΠΑ

Συνθετική Προσέγγιση για την Διαστερεοεκλεκτική Ανάπτυξη Διαμορφωτικά Περιορισμένων Φωσφινικών Διπεπτιδίων

Greek

Synthetic Approach to the Diastereoselective Development of Conformationally Restricted Phosphinic Dipeptides

The introduction of structural elements that confer conformational restriction
in the mobility of bioactive peptides and pseudopeptides can stabililize
specific conformations in the molecule which adapt ideally into the
complementary active site of an enzyme. The major difficulty concerning the
synthesis of the structures of formula II lies in the stereochemical control of
the three stereogenic centers of the five-membered carbocyclic ring.
In this work, we describe the design and synthesis of conformationally
restricted phosphinic peptides bearing substituted pseudoproline residues in
their P1΄ position. The use of the Evans oxazolidinone bearing the benzydryl
group is the main factor that induces diastereoselectivity in the allylic
substitution reaction. The introduction of two identical R groups in the
5-position of oxazolidinone 2, or respectively the replacement of Ο by S aiming
to optimal diastereoselectivity in the allylic substitution and 1,4-conjugate
addition of the vinylmagnesiumcuprate reagent was also explored. Subsequently,
the behavior of the compounds of type VII during the removal of the chiral
auxiliary was investigated. Finally, the synthesis of a
stereochemically-defined phosphinic precursor allowing broad differentiation
was pursued.

Organic Synthesis, Conformational Restriction, Oxazolidinone, Thiazolidinone, Phosphinic Acid

Yes

1-10

Yes

94

121

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https://pergamos.lib.uoa.gr/uoa/dl/object/1319869