- Total Synthesis of Paclitaxel
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The total synthesis of paclitaxel (Taxol) is described. Double Rubottom oxidation of the bis(silyl enol ether) derived from a tricarbocyclic diketone effectively installed a bridgehead olefin and C-5/C-13 hydroxy groups in a one-step operation. The novel Ag-promoted oxetane formation smoothly constructed the tetracyclic framework of paclitaxel.
- Iiyama, Shota,Fukaya, Keisuke,Yamaguchi, Yu,Watanabe, Ami,Yamamoto, Hiroaki,Mochizuki, Shota,Saio, Ryosuke,Noguchi, Takashi,Oishi, Takeshi,Sato, Takaaki,Chida, Noritaka
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p. 202 - 206
(2021/12/27)
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- Paclitaxel derivative and preparation method thereof
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The invention discloses a paclitaxel derivative and a preparation method thereof, and belongs to the field of preparation of taxanes anticancer drugs, and the taxol derivative is 2 -benzoyl -2 -aspianoyl paclitaxel and the preparation method comprises dis
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Paragraph 0032-0034; 0043-0044; 0048-0049
(2021/11/10)
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- PROCESS FOR PREPARING TAXOIDS FROM BACCATIN DERIVATIVES USING LEWIS ACID CATALYST
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The present invention relates to a process of preparing a taxoid (X) by reacting a protected baccatin derivative (B) with a β-lactam (C) in the presence of one or more Lewis acids and a base agent. The present invention also relates to a process of preparing the protected baccatin derivative (B) from a baccatin derivative (A) comprising a protection reaction catalyzed by one or more Lewis acids with an optional base agent.
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- PROCESSES FOR PREPARATION OF TAXANES AND INTERMEDIATES THEREOF
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A paclitaxel intermediate of formula 1: wherein R1 is acetyl, R2 is tert-butyloxycarbonyl (BOC), R3 and R4 are phenyl and R5 is 1-ethoxyethyl, is provided. Also provided are processes for preparing taxane intermediates of formula 1 comprising reacting a compound of formula 2 with a compound of formula 3 wherein, R1, R2 and R5 are independently a hydroxyl protecting group; R3 is phenyl, substituted phenyl, a straight or branched alkyl containing 1 to 12 carbon atoms, alkenyl containing 2 to 12 carbon atoms, cycloalkyl containing 4 to 15 carbon atoms, cycloalkenyl or an R6—O— group in which R6 is: phenyl, substituted phenyl group, a C1-C8 straight or branched alkyl, a C2-C8 straight or branched alkenyl group, a C3-C8 straight or branched alkynyl, a C3-C7 cycloalkyl, C4-C7 cycloalkenyl, a C7-C11 bicycloalkyl substituent, or a saturated or unsaturated nitrogen; and R4 is phenyl or a substituted phenyl group.
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Page/Page column 12
(2009/12/05)
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- Beta-Lactams useful for preparation of substituted isoserine esters using metal alkoxides
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β-lactams are disclosed which are useful for preparing N-acyl, N-sulfonyl and N-phosphoryl substituted esters by reaction with a metal alkoxide.
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- Synthesis and biological evaluation of 2-acyl analogues of paclitaxel (Taxol)
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The anticancer drug paclitaxel (Taxol) has been converted to a large number of 2-debenzoyl-2-aroyl derivatives by three different methods. The bioactivities of the resulting analogues were determined in both tubulin polymerization and cytotoxicity assays, and several analogues with enhanced activity as compared with paclitaxel were discovered. Correlation of cytotoxicity in three cell lines with tubulin polymerization activity showed reasonable agreement. Among the cell lines examined, the closest correlation with antitubulin activity was observed with a human ovarian carcinoma cell line.
- Kingston, David G. I.,Chaudhary, Ashok G.,Chordia, Mahendra D.,Gharpure, Milind,Gunatilaka, A. A. Leslie,Higgs, Paul I.,Rimoldi, John M.,Samala, Lakshman,Jagtap, Prakash G.,Giannakakou, Paraskevi,Jiang, Yuan Q.,Lin, Chii M.,Hamel, Ernest,Long, Byron H.,Fairchild, Craig R.,Johnston, Kathy A.
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p. 3715 - 3726
(2007/10/03)
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- Synthesis and biological activity of A-nor-paclitaxel analogues
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A number of paclitaxel analogues with a 5-membered A-ring (A-nor-paclitaxels, or (15→1)-abeo-paclitaxels) have been prepared in order to determine whether analogues of this class might have improved bioactivity as compared with paclitaxel. Most of the com
- Chordia, Mahendra D.,Kingston, David G. I.,Hamel, Ernest,Lin, Chii M.,Long, Byron H.,Fairchild, Craig A.,Johnston, Kathy A.,Rose, William C.
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p. 941 - 947
(2007/10/03)
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- Preparation of substituted isoserine esters using β-lactams and metal or ammonium alkoxides
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A process for preparing N-acyl, N-sulfonyl and N-phosphoryl substituted isoserine esters in which a metal or an ammonium alkoxide is reacted with a β-lactam.
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- Total synthesis of Taxol. 1. Retrosynthesis, degradation, and reconstitution
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A successful strategy for the enantioselective synthesis of the natural stereoisomer of Taxol (1) has been developed. This strategy utilized the convergent assembly of Taxol's central eight-membered B ring from preformed synthons for rings A (10) and C (9) followed by late introduction of the D ring and side chain. Degradative studies confirmed the viability of certain crucial manipulations including oxidation of the C13 position (35 → 3) and regioselective introduction of the C1-hydroxyl, C2-benzoyloxy moiety (29 → 31). Additionally, a convenient method for the large-scale production of 29, a derivative useful for C2 analog production, was developed.
- Nicolaou,Nantermet,Ueno,Guy,Couladouros,Sorensen
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p. 624 - 633
(2007/10/02)
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- Novel chemistry of taxol: Retrosynthetic and synthetic studies
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10-Deacetyl baccatin III was used in the synthesis of compounds, all of which were converted to Taxol via efficient synthetic pathways
- Nicolaou,Nantermet,Ueno,Guy
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p. 295 - 296
(2007/10/02)
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- Metal alkoxides
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A metal alkoxide having the following formula: STR1 wherein T1 is hydrogen or a hydroxy protecting group, Z is --OT2, or --OCOCH3, T2 is hydrogen or a hydroxy protecting group, and M is selected from the group c
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