Biomedical Engineering Reference
In-Depth Information
SCHEME 6.8
Selected proline analogs as building blocks for the generation of skeletal
diversity through RCM reaction in the B/C/P approach.
pairing phase with ring-closing metathesis (RCM) reactions (Schemes 6.8 and 6.9).
The B/C/P strategy devised allowed for the generation of a small library of fragments
possessing diverse skeletal structures and rich in stereochemical variation, thanks to
the use of different stereoisomers as starting building blocks for synthesis.
6.4.3 Scaffolds from Amino Aldehyde Intermediates
The field of peptidomimetics has taken advantage of iminium chemistry for the
generation of suitable scaffolds possessing amino acid moieties, taking advantage of
the amino group and the carbonyl resulting from manipulation of the carboxylic acid
of the amino acids. In particular, resin-bound amino acids have attracted considerable
attention for their use in synthetic methods consisting of functionalization of the amine
moiety, followed by cyclative cleavage to access the target scaffolds.
Accordingly, an interesting paper by Scott et al. described an entry to skeletal
diversity by exploiting the chemistry of resin-bound amino aldehydes deriving from
-amino acids [25]. In this paper, the authors reported the preparation, via solid-phase
