TY - JOUR
T1 - The Dolastatins. 19. Synthesis of Dolaisoleuine
AU - Pettit, George
AU - Singh, Sheo Bux
AU - Srirangam, Jayaram K.
AU - Hogan-Pierson, Fiona
AU - Williams, Michael D.
PY - 1994/4/1
Y1 - 1994/4/1
N2 - The synthesis of dolaisoleuine as its ieri-butyl ester (Dil-OBut), a β-methoxy-γ-amino acid component of dolastatin 10, has been achieved employing as key step an aldol condensation between. N-(benzyloxycarbonyl)-N-methyl-(S,S)-isoleucinaland ieri-butyl acetate followed by O-methylation. The overall six-step reaction sequence to Dil proved to be convenient for routine preparation of this new amino acid and its stereochemical assignment as (3R,4S,5S)-N,O-dimethylisostatine.
AB - The synthesis of dolaisoleuine as its ieri-butyl ester (Dil-OBut), a β-methoxy-γ-amino acid component of dolastatin 10, has been achieved employing as key step an aldol condensation between. N-(benzyloxycarbonyl)-N-methyl-(S,S)-isoleucinaland ieri-butyl acetate followed by O-methylation. The overall six-step reaction sequence to Dil proved to be convenient for routine preparation of this new amino acid and its stereochemical assignment as (3R,4S,5S)-N,O-dimethylisostatine.
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U2 - 10.1021/jo00086a034
DO - 10.1021/jo00086a034
M3 - Article
AN - SCOPUS:0028226107
SN - 0022-3263
VL - 59
SP - 1796
EP - 1800
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 7
ER -