Pregled bibliografske jedinice broj: 254701
New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method
New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method // Tetrahedron, 48 (1992), 34; 6985-7012 doi:10.1016/S0040-4020(01)91210-4 (međunarodna recenzija, članak, znanstveni)
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Naslov
New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method
Autori
Ojima, Iwao ; Habuš, Ivan ; Zhao, Mangzhu ; Zucco, Martine ; Park, Young Hoon ; Sun, Chung Ming ; Brigaud, Thierry
Izvornik
Tetrahedron (0040-4020) 48
(1992), 34;
6985-7012
Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni
Ključne riječi
chiral ester ; enolate-imine ; taxol
Sažetak
Highly efficient 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 enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R, 3S)-3- phenyl-isoserine and its analogs. (3R, 4S)-N-benzoyl- 3-(1-ethoxyethoxy)-4-phenyl-2- azetidinone readily derived from the 3-hydroxy-4-phenyl-β -lactam is coupled with protected baccatin IIIs, followed by deprotection to give optically pure taxol and 10- deacetyl-7, 10-bis(Troc)-taxol in good yields. Fully assigned 1H, 13C, and 2D (COSY and HETCOR) NMR spectra of taxol thus synthesized are shown and discussed.
Izvorni jezik
Engleski
Znanstvena područja
Kemija
Citiraj ovu publikaciju:
Časopis indeksira:
- Web of Science Core Collection (WoSCC)
- Science Citation Index Expanded (SCI-EXP)
- SCI-EXP, SSCI i/ili A&HCI
- Scopus
