Asymmetric nitroaldol reaction. Synthesis of taxotere side chain and (-)-bestatin using (1R)-8-phenylmenthyl glyoxylate

Iwona Kudyba; Jerzy Raczko; Janusz Jurczak

doi:10.1021/jo0358269

Asymmetric nitroaldol reaction. Synthesis of taxotere side chain and (-)-bestatin using (1R)-8-phenylmenthyl glyoxylate

J Org Chem. 2004 Apr 16;69(8):2844-50. doi: 10.1021/jo0358269.

Authors

Iwona Kudyba¹, Jerzy Raczko, Janusz Jurczak

Affiliation

¹ Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.

PMID: 15074936
DOI: 10.1021/jo0358269

Abstract

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.