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Studies towards the synthesis of bicyclomycin precursors: Synthesis of N,N ′‐disubstituted 2,5‐diketopiperazines in solution and on solid phase
Author(s) -
Fryszkowska Anna,
Ostaszewski Ryszard
Publication year - 2008
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570450321
Subject(s) - diketopiperazines , chemistry , aldehyde , acetal , combinatorial chemistry , stereochemistry , solid phase synthesis , organic chemistry , catalysis , peptide , biochemistry
The synthesis of 3‐(hydroxyalkyl)‐ N,N ′‐disubstituted 2,5‐diketopiperazine derivatives ‐ compounds required for the bicyclomycin analogues preparation ‐ has been studied. The use of various oxo components in the Ugi multicomponent reaction (U‐MCR) has been evaluated. The first example of an semicyclic O,O ‐acetal employed as an aldehyde equivalent in the U‐MCR has been reported. The preparation and the synthetic application of Wang resin‐bound aliphatic aldehydes in the synthesis of 2,5‐diketopiperazine skeleton has also been described.