Asymmetric Sulfur Ylide Mediated Aziridination: Application in the Synthesis of the Side Chain of Taxol
(Formula presented). Sulfur ylide methodology has been used to construct the Taxol side chain with a high degree of enantioselectivity via a trans-aziridine followed by stereospecific rearrangement of the trans-benzoylaziridine into a trans-oxazoline.
Aggarwal, Varinder K.,Vasse, Jean-Luc
p. 3987 - 3990
(2007/10/03)
Chemoenzymatic Synthesis of the C-13 Side Chain of Taxol: Optically Active 3-Hydroxy-4-phenyl β-Lactam Derivatives
Enantiomerically pure 3-hydroxy-4-phenyl β-lactam derivatives have been successfully prepared via enantioselective hydrolyses and transesterifications of racemic esters and alcohols respectivily catalyzed by bacterial lipases.These lipases also catalyzed highly enantioselective cleavage of the β-lactam ring of (+/-)-10 to yield derivatives of (2R,3S)-phenylisoserine in high enantiomeric excess.The resolved enantiomers are important intermediates in the synthesis of the C-13 side chain of taxol.
Brieva, Rosario,Crich, Joyce Z.,Sih, Charles J.
p. 1068 - 1075
(2007/10/02)
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