261968-20-1Relevant academic research and scientific papers
Probing o-diphenylphosphanyl benzoate (o-DPPB)-directed C - C bond formation: Total synthesis of dictyostatin
Wünsch, Sebastian,Breit, Bernhard
supporting information, p. 2358 - 2363 (2015/02/05)
Herein, we report a robust total synthesis of dictyostatin. This polyketide natural product has attracted much attention because of its impressive antiproliferative activity against several human cancer-cell lines. We accomplished its synthesis in a highly convergent manner from three fragments of equal complexity, which were prepared on multigram scale. The southern and northwestern subunits were constructed through application of our o-DPPB-directed hydroformylation and allylic substitution methodology, respectively. These methods generated the C6 and C14 stereocenters of dictyostatin with good diastereoselectivities and simultaneously allowed further elaboration of the fragments by Wittig olefination and Sharpless asymmetric epoxidation, respectively. The compelling performance of the hydroformylation and allylic substitution with regard to practicability, selectivity, and scale underline their value for the construction of propionate motifs.
A second-generation total synthesis of (+)-discodermolide: The development of a practical route using solely substrate-based stereocontrol
Paterson, Ian,Delgado, Oscar,Florence, Gordon J.,Lyothier, Isabelle,O'Brien, Matthew,Scott, Jeremy P.,Sereinig, Natascha
, p. 150 - 160 (2007/10/03)
(Chemical Equation Presented). A novel total synthesis of the complex polyketide (+)-discodermolide, a promising anticancer agent of sponge origin, has been completed in 7.8% overall yield over 24 linear steps, with 35 steps altogether. This second-genera
Synthesis and biological assessment of simplified analogues of the potent microtubule stabilizer (+)-discodermolide
Minguez, Jose M.,Kim, Sun-Young,Giuliano, Kenneth A.,Balachandran, Raghavan,Madiraju, Charitha,Day, Billy W.,Curran, Dennis P.
, p. 3335 - 3357 (2007/10/03)
An efficient, convergent and stereocontrolled synthesis of simplified analogues of the potent antimitotic agent (+)-discodermolide has been achieved and several small libraries have been prepared. In all the libraries, the discodermolide methyl groups at
1,6-asymmetric induction in boron-mediated aldol reactions: application to a practical total synthesis of (+)-discodermolide.
Paterson, Ian,Delgado, Oscar,Florence, Gordon J,Lyothier, Isabelle,Scott, Jeremy P,Sereinig, Natascha
, p. 35 - 38 (2007/10/03)
By relying solely on substrate-based stereocontrol, a practical total synthesis of the microtubule-stabilizing anticancer agent (+)-discodermolide has been realized. This exploits a novel aldol bond construction with 1,6-stereoinduction from the boron eno
Certain substituted polyketides, pharmac eutical compositions containing them and their use in treating tumors
-
, (2008/06/13)
The present invention relates to certain substituted polyketides of formula I, wherein A, B and C are as defined herein, pharmaceutical compositions containing said compounds, and the use of said compounds in treating tumors.
Simultaneous preparation of four truncated analogues of discodermolide by fluorous mixture synthesis
Curran, Dennis P.,Furukawa, Takashi
, p. 2233 - 2235 (2007/10/03)
(matrix presented) Four analogues made in one synthesis Four truncated analogues of the natural product discodermolide were synthesized in a single synthetic sequence. Precursors bearing four different groups at C22, each with a unique fluorous p-methoxyb
A practical synthesis of (+)-discodermolide and analogues: Fragment union by complex aldol reactions
Paterson,Florence,Gerlach,Scott,Sereinig
, p. 9535 - 9544 (2007/10/03)
A practical stereocontrolled synthesis of (+)-discodermolide (1) has been completed in 10.3% overall yield (23 steps longest linear sequence). The absolute stereochemistry of the C1-C6 (7), C9-C16 (8), and Csub
Total synthesis of the antimicrotubule agent (+)-discodermolide using boron-mediated aldol reactions of chiral ketones
Paterson, Ian,Florence, Gordon J.,Gerlach, Kai,Scott, Jeremy P.
, p. 377 - 380 (2007/10/03)
With a similar mechanism of action to taxol, the title compound 1 is a particularly promising candidate for development in cancer chemotherapy. This efficient synthesis, based on stereocontrolled aldol reactions, should help to overcome the scarce natural
Syntheses of discodermolides useful for investigating microtubule binding and stabilization
Hung, Deborah T.,Nerenberg, Jennie B.,Schreiber, Stuart L.
, p. 11054 - 11080 (2007/10/03)
Discodermolide is a marine natural product reported to inhibit the proliferation of T cells and exhibit immunosuppresive activity. Total syntheses of the natural antipode of discodermolide and several variants are reported. These studies provide reagents
