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A 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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