155588-13-9Relevant academic research and scientific papers
Formal total synthesis of (-)-taxol through Pd-catalyzed eight-membered carbocyclic ring formation
Hirai, Sho,Utsugi, Masayuki,Iwamoto, Mitsuhiro,Nakada, Masahisa
supporting information, p. 355 - 359 (2015/02/19)
A formal total synthesis of (-)-taxol by a convergent approach utilizing Pd-catalyzed intramolecular alkenylation is described. Formation of the eight-membered carbocyclic ring has been a problem in the convergent total synthesis of taxol but it was solved by the Pd-catalyzed intramolecular alkenylation of a methyl ketone affording the cyclized product in excellent yield (97 %), indicating the high efficiency of the Pd-catalyzed intramolecular alkenylation. Rearrangement of the epoxy benzyl ether through a 1,5-hydride shift, generating the C3 stereogenic center and subsequently forming the C1-C2 benzylidene, was discovered and utilized in the preparation of a substrate for the Pd-catalyzed reaction.
Synthetic studies with 13-deoxybaccatin III
Ahn, Yu Mi,Vander Velde, David G.,Georg, Gunda I.
, p. 7140 - 7143 (2007/10/03)
An efficient synthesis of 13-epi-7-O-(triethylsilyl)baccatin III from 13-deoxybaccatin III is described. Oxidation of 13-deoxy-7-O-(triethylsilyl)baccatin III with tert-butyl peroxide, followed by reduction with SmI2, produced 13-epi-7-O-(triethylsilyl)baccatin III in good overall yield. The preparation of 13-oxo-7-O-(triethylsilyl)baccatin III from 13-epi-7-O-(triethylsilyl)baccatin III using tetrapropylammonium perruthenate and N-methylmorpholine N-oxide is also reported.
Total synthesis of baccatin III and taxol
Danishefsky, Samuel J.,Masters, John J.,Young, Wendy B.,Link,Snyder, Lawrence B.,Magee, Thomas V.,Jung, David K.,Isaacs, Richard C. A.,Bornmann, William G.,Alaimo, Cheryl A.,Coburn, Craig A.,Di Grandi, Martin J.
, p. 2843 - 2859 (2007/10/03)
An intramolecular Heck reaction (90 → 91) serves as the key step in the total synthesis of the titled compounds. The synthetic route is based on utilizing the Wieland-Miescher ketone (5) 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 (6). Catalytically induced enantiotopic control and early emplacement of the oxetane are other features of the route.
Total synthesis of Taxol. 1. Retrosynthesis, degradation, and reconstitution
Nicolaou,Nantermet,Ueno,Guy,Couladouros,Sorensen
, p. 624 - 633 (2007/10/02)
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.
Eine Totalsynthese von Taxol
Masters, John J.,Link, J. T.,Snyder, Lawrence B.,Young, Wendy B.,Danishefsky, Samuel J.
, p. 1886 - 1888 (2007/10/03)
Keywords: Baccatin III; Heck-Reaktionen; Taxol; Totalsynthesen
Novel chemistry of taxol: Retrosynthetic and synthetic studies
Nicolaou,Nantermet,Ueno,Guy
, p. 295 - 296 (2007/10/02)
10-Deacetyl baccatin III was used in the synthesis of compounds, all of which were converted to Taxol via efficient synthetic pathways
