ChemInform Abstract: Asymmetric Synthesis of the Taxol and Taxotere C-13 Side Chains.

ChemInform ◽  
2010 ◽  
Vol 26 (8) ◽  
pp. no-no
Author(s):  
M. E. BUNNAGE ◽  
S. G. DAVIES ◽  
C. J. GOODWIN
Keyword(s):  
Asymmetric Synthesis ◽  
Side Chains

Asymmetric synthesis of taxol arid taxotère side chains by enolate hydroxylation

1996 ◽  
Vol 74 (4) ◽  
pp. 621-624 ◽  
Author(s):  
Stephen Hanessian ◽  
Jean-Yves Sancéau
Keyword(s):  
Asymmetric Synthesis ◽  
Key Words ◽  
Side Chains ◽  
Key Words Taxol ◽  
Phosphoric Triamide ◽  
Enolate Hydroxylation

We report an asymmetric synthesis of the taxol and taxotère side chains by hydroxylation of enolates derived from N-substitued methyl 3-amino-3-phenyl propionate with the oxodiperoxymolybdenum (pyridine) (hexamethyl phosphoric triamide) complex (MoOPH). Key words: taxol and taxotère side chains, hydroxylation.

Asymmetric Synthesis of Helically Stable Poly(quinoxaline-2,3-diyl)s Having Hydrophilic and/or Hydrophobic Side Chains

1998 ◽  
Vol 31 (5) ◽  
pp. 1697-1699 ◽  
Author(s):  
Yoshihiko Ito ◽  
Toshiyuki Miyake ◽  
Takafumi Ohara ◽  
Michinori Suginome
Keyword(s):  
Asymmetric Synthesis ◽  
Side Chains

scholarly journals 2-Phenyl-tetrahydropyrimidine-4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids

2009 ◽  
Vol 5 ◽  
Author(s):  
Markus Nahrwold ◽  
Arvydas Stončius ◽  
Anna Penner ◽  
Beate Neumann ◽  
Hans-Georg Stammler ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Side Chains ◽  
Acid Labile

Novel procedures have been developed to condense benzaldehyde effectively with β-amino acid amides to cyclic benzyl aminals. Double carbamate protection of the heterocycle resulted in fully protected chiral β-alanine derivatives. These serve as universal precursors for the asymmetric synthesis of functionalised β2-amino acids containing acid-labile protected side chains. Diastereoselective alkylation of the tetrahydropyrimidinone is followed by a chemoselective two step degradation of the heterocycle to release the free β2-amino acid. In the course of this study, an L-asparagine derivative was condensed with benzaldehyde and subsequently converted to orthogonally protected (R)-β2-homoaspartate.

Previously published / Prédémment paruAsymmetric total synthesis of (+)-exo-brevicomin based on enantioconvergent biocatalytic hydrolysis of an alkene-functionalized 2,3-disubstituted epoxide

2002 ◽  
Vol 80 (6) ◽  
Author(s):  
Sandra F Mayer ◽  
Harald Mang ◽  
Andreas Steinreiber ◽  
Robert Saf ◽  
Kurt Faber
Keyword(s):  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Bark Beetle ◽  
Epoxide Hydrolase ◽  
Side Chains ◽  
Beetle Species ◽  
Epoxide Hydrolases ◽  
Pheromone System ◽  
Enantioconvergent Hydrolysis ◽  
Hydrolysis Of

A short total asymmetric synthesis of (+)-exo- and (–)-endo-brevicomin ((+)-exo-3 and (–)-endo-3), which are components of the attracting pheromone system of several bark-beetle species belonging to the genera Dendroctonus and Dryocoetes, was accomplished via a chemoenzymatic protocol. The key step consisted of biocatalytic hydrolysis by bacterial epoxide hydrolases of cis-configured 2,3-disubstituted oxiranes bearing olefinic side chains. This reaction proceeded in an enantioconvergent fashion, by affording a single enantiomeric vic-diol from the rac-epoxide in up to 92% ee and 83% isolated yield.Key words: bacterial epoxide hydrolase, 2,3-disubstituted oxirane, enantioconvergent hydrolysis, (+)-exo-brevicomin, (–)-endo-brevicomin.

Asymmetric synthesis of novel α-amino acids with β-branched side chains

2007 ◽  
Vol 17 (9) ◽  
pp. 2401-2403 ◽  
Author(s):  
Minsheng Zhang ◽  
Alex Porte ◽  
George Diamantidis ◽  
Kimberly Sogi ◽  
Dennis Kubrak ◽  
...  
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Side Chains

Asymmetric Synthesis of 3-Substituted Proline Chimeras Bearing Polar Side Chains of Proteinogenic Amino Acids

2004 ◽  
Vol 69 (23) ◽  
pp. 7940-7948 ◽  
Author(s):  
Jean Quancard ◽  
Aurélie Labonne ◽  
Yves Jacquot ◽  
Gérard Chassaing ◽  
Solange Lavielle ◽  
...  
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Side Chains
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