Asymmetric Nitroaldol Reaction. Synthesis of Taxotere Side Chain and (−)-Bestatin Using (1R)-8-Phenylmenthyl Glyoxylate
- 12 March 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (8) , 2844-2850
- https://doi.org/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.Keywords
This publication has 57 references indexed in Scilit:
- Asymmetric Synthesis of β-Amino-α-Hydroxy Acids through Lewis Acid-Mediated Addition of Ketene Acetal to IminesBulletin of the Chemical Society of Japan, 2001
- A Highly Efficient Aminohydroxylation ProcessAngewandte Chemie International Edition in English, 1997
- Asymmetric synthesis of building-blocks for peptides and peptidomimetics by means of the β-lactam synthon methodChemical Society Reviews, 1997
- A Catalytic Asymmetric Synthesis of CyclohexylnorstatineThe Journal of Organic Chemistry, 1996
- A novel asymmetric synthesis of cis-3-hydroxy-4-aryl azetidin-2-onesBioorganic & Medicinal Chemistry Letters, 1993
- An efficient semisynthesis of taxol from (3R,4S)-N-Benzoyl-3-[(t-butyldimethylsilyl)oxy]-4-phenyl-2-azetidinone and 7-(Triethylsilyl)baccatin IIIBioorganic & Medicinal Chemistry Letters, 1993
- A practical chemoenzymic synthesis of the taxol C-13 side chain N-benzoyl-(2R,3S)-3-phenylisoserineThe Journal of Organic Chemistry, 1993
- A practical, highly enantioselective synthesis of the taxol side chain via asymmetric catalysis.The Journal of Organic Chemistry, 1992
- A Novel Synthesis of Cyclohexylnorstatine Isopropyl Ester, the C-Terminal Component of a Renin InhibitorHETEROCYCLES, 1990
- An efficient, enantioselective synthesis of the taxol side chainThe Journal of Organic Chemistry, 1986