| Abstract
| - The enantioselective synthesis of cyclopentanedicarboxylic amino acid 1, a novel rigid and functionalizedl-glutamic acid analogue, has been achieved in 15 linearsteps from silyloxypyrrole 3, utilizing l-glyceraldehyde 4 asthe source of chirality. The key steps in the synthesis arethree sequential aldol-based carbon−carbon bond-formingreactions: two crossed vinylogous aldol additions (2 + 3 →8 and 4 + 5 → 10 + 11) and one intramolecular silylativealdolization (6 → 7). En passant, the short syntheses of (2S)-2-hydroxymethylglutamic acid (16) and its (2R)-enantiomerent-16, a potent metabotropic glutamate receptor agonist,have been achieved.
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