173073-98-8Relevant academic research and scientific papers
Concise synthesis of pentenyl phenyl acrylic acid
Sun, Dequn,Lai, Pengxiang,Xie, Weidong,Deng, Jingen,Jiang, Yaozhong
, p. 2989 - 2994 (2007)
Pentenyl phenyl acrylic acid is a structural unit of pepticinnamin E, a natural product and a bisubstrate inhibitor of FPTase. In this article, a new synthetic strategy was developed to prepare pentenyl phenyl acrylic acid with high stereoselectivity and
A novel water-soluble m-TPPTC ligand: Steric and electronic features - Recent developments in Pd- and Rh-catalyzed C-C bond formations
Genin, Emilie,Amengual, Remi,Michelet, Veronique,Savignac, Monique,Jutand, Anny,Neuville, Luc,Genet, Jean-Pierre
, p. 1733 - 1741 (2007/10/03)
The steric and electronic features of the novel water-soluble phosphane m-TPPTC have been determined using NMR, IR and UV-VIS spectroscopic methods and compared to the well-known sulfonated analogue TPPTS. The higher basicity of m-TPPTC compared to TPPTS
Taxane synthesis through intramolecular pinacol coupling at C-1 - C-2. Highly oxygenated C-aromatic taxanes
Swindell, Charles S.,Fan, Weiming
, p. 1109 - 1118 (2007/10/03)
Chiral, nonracemic intramolecular pinacol coupling substrates 3/20 and 30 have been prepared from ethyl isopropyl ketone and acryloyl chloride, which provide the A-ring and either o-iodobenzyl alcohol or 2,4-dimethoxybenzyl alcohol, which provide the respective aromatic C-rings, in 14-16 linear steps in overall yields of approximately 20%. Potential pinacol coupling substrate 23 could not be made available for investigation due to intervening pinacol rearrangement in the acetonide formation step. 3/20 undergo stereoselective cyclizations mediated by TiCl4-Zn in which the C-9 oxygen substituent plays the dominant role in determining the stereochemical outcome at C-1 and C-2 in the respective tricyclic products 4 and 21. The formation of 21 is the more stereoselective process. The reagent of choice for the transformation of 30 into 31 is SmI2, which, although less stereoselective than TiCl4-Zn, leads to higher yielding carbon-carbon bond formation relative to carbonyl reduction. These pinacol cyclizations are interpreted to occur through endo boat-chair transition structures that prefer to orient the developing C-2 substituent and the preexisting C-9 substituent equatorially. Pinacol product 31 was converted through three additional steps into 40 having a B-ring closely related to that of taxol. We believe that these studies indicate pinacol cyclizations at C-1-C-2 to have considerable potential for producing advanced intermediates for syntheses of taxol and related complex taxanes.
