Journal ArticleDOI
Efficient and practical asymmetric synthesis of the taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenylisoserine, and its analogs via chiral 3-hydroxy-4-aryl-.beta.-lactams through chiral ester enolate-imine cyclocondensation
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TLDR
A highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-β-lactams with >96% ee is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenylisoserine, and its analogues.Abstract:
A highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-β-lactams with >96% ee is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenylisoserine, and its analoguesread more
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Journal ArticleDOI
Chemistry and Biology of Taxol
TL;DR: This account attempts to bring together in a cogent overview the chemistry and biology of taxol, one of the few organic compounds, which, like benzene and aspirin, is recognizable by name to the average citizen.
Journal ArticleDOI
Taxol and taxotere: discovery, chemistry, and structure-activity relationships
Journal ArticleDOI
New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method
Iwao Ojima,Ivan Habus,Mangzhu Zhao,Martine Zucco,Young Hoon Park,Chung-Ming Sun,Thierry Brigaud +6 more
TL;DR: In this paper, a chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-β-lactams with excellent enantiomeric purity is successfully applied to the asymmetric synthesis of the enantiomersically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenyl-isoserine and its analogs.
Journal ArticleDOI
Total Synthesis of Baccatin III and Taxol
Samuel J. Danishefsky, , a,b John J. Masters,c Wendy B. Young,e Lawrence B. Snyder,f Thomas V. Magee,g David K. Jung,h Richard C. A. Isaacs,William Bornmann,i Cheryl A. Alaimo,h and Craig A. Coburn,Martin J. Di Grandi i +10 more
TL;DR: In this paper, the Wieland−Miescher ketone was used as a matrix to provide the C and D rings of the targets and to provide functionality implements for joining this sector to an A ring precursor.