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Detail
BukuA synthetic approach toward paclitaxel analogs from (S)-(+)-carvone
Bibliografi
Author: Lo, Ho Yin ; Shing, T.K.M. (Advisor)
Topik: CHEMISTRY; ORGANIC
Bahasa: (EN )    ISBN: 0-599-69299-5    
Penerbit: CHINESE UNIVERSITY OF HONG KONG (PEOPLE'S REPUBLIC OF CHINA)     Tahun Terbit: 2000    
Jenis: Theses - Dissertation
Fulltext: 9964828.pdf (0.0B; 0 download)
Abstract
In this thesis, a review concerning the development of the clinical drug Paclitaxel (Taxol®) and the chemical syntheses of this natural product from 1960 to 1999 is presented. Synthetic studies on the construction of Paclitaxel ABC-ring skeleton via the type 2 Intramolecular Diels-Alder (IMDA) reaction are described. The synthesis adopts a C→ABC ring formation strategy. Three kinds of precursors (a precursor with electron deficient diene, a precursor with normal electronic demand, and a precursor with electron deficient dienophile) were synthesised from R-(–)-carvone and S-(+)-carvone through an acid catalysed intermolecular Diels-Alder reaction with isoprene. The investigation of the type 2 IMDA reaction reveals the importance of the C-2 ketone and the problem of elimination reaction of the C-10 benzyl group during the reaction, leading to undesirable side products.
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