"Diversity oriented synthesis" of functionalized chiral tetrahydropyridines: potential GABA receptor agonists and azasugars from natural amino acids via a sequential Baylis-Hillman reaction and RCM protocol.
The preparation of chiral tetrahydropyridine-4-carboxylates as isoguvacine analogues and azasugars with a tertiary stereocenter from L-amino acids via diastereoselective a Baylis-Hillman reaction of N-allyl-Boc alpha-aminal, followed by ring-closing metathesis and dihydroxylation sequences, is reported.
Krishna
Palakodety Radha
PR
D-206/B, Discovery Laboratory, Organic Chemistry Division III, Indian Institute of Chemical Technology, Hyderabad 500 007, India. prkgenius@iict.res.in
Reddy
P Srinivas
PS
D000596:Amino Acids / Q000737:chemistry*; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D018755:GABA Agonists / Q000138:chemical synthesis* / Q000737:chemistry; D007539:Isonicotinic Acids / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D001372:Aza Compounds; D018755:GABA Agonists; D007539:Isonicotinic Acids; D011725:Pyridines; C015300:isoguvacine