Asymmetric nitroaldol reaction. Synthesis of taxotere side chain and (-)-bestatin using (1R)-8-phenylmenthyl glyoxylate.
The nitroaldol reaction of (1R)-8-phenylmenthyl glyoxylate (3b) with 1-nitro-1-phenylmethane (4) or with 1-nitro-2-phenylethane (13) led stereoselectively to adducts syn-2b and syn-12b, which were then transformed into the Taxotere side chain and (-)-bestatin hydrochloride in overall yields of 52% and 31%, respectively.
Kudyba
Iwona
I
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
Raczko
Jerzy
J
Jurczak
Janusz
J