211426-31-2Relevant academic research and scientific papers
Formal synthesis of natural epibatidine and of its enantiomer: Use of radical cyclization in an enantiospecific route
Clive, Derrick L. J.,Yeh, Vince S. C.
, p. 4789 - 4792 (2007/10/03)
(S)-Pyroglutamic acid was converted into the (phenylthio)acetylene 14, which undergoes radical cyclization to the 7-azabicyclo[2.2.1]heptane 15. Ozonolysis then affords ketone 4, a synthetic precursor of (-)-epibatidine.
A highly stereocontrolled asymmetric synthesis of the Taxol C-13 side chain; (4S, 5R)-2,4-Diphenyloxazoline-5 carboxylic acid
Lee, Kee-Young,Kim, Yong-Hyun,Park, Min-Sung,Ham, Won-Hun
, p. 8129 - 8132 (2007/10/03)
A stereoselective synthesis of (4S, 5R)-2,4-diphenyloxaline-5-carboxylic acid, a precursor of the Taxol C-13 side chain was achieved using palladium- catalyzed oxazoline formation reaction from commercially available amino acid.
Two distinct epoxide ring opening pathways in a monocyclic model system of the kedarcidin chromophore
Dai, Wei-Min,Wu, Jinlong,Wu, Anxin
, p. 4091 - 4094 (2007/10/03)
Two monocyclic model compounds 2 and 3 were synthesized from (Z)- ketoeneyne 5 for studying the epoxide ring opening pathways related to activation of the kedarcidin chromosphore (1). The solvent-derived SNI products 8a,b and 9a,b were formed from 2 and 3 in MeOH while the S(N)2 products 10a,b were produced from 2 and 3 with methyl thioglycolate in buffer (pH 7.0)-iPrOH; the latter reaction may provide a new scenario for bioreductive activation of the kedarcidin chromophore via an S(N)2 attack of thiol at the propargylic carbon atom.
