756834-76-1Relevant academic research and scientific papers
Spiroacetal formation through telescoped cycloaddition and carbon-hydrogen bond functionalization: Total synthesis of bistramide A
Han, Xun,Floreancig, Paul E.
supporting information, p. 11075 - 11078 (2015/03/30)
Spiroacetals can be formed through a one-pot sequence of a hetero-Diels-Alder reaction an oxidative carbon-hydrogen bond cleavage and an acid treatment. This convergent approach expedites access to a complex molecular subunit which is present in numerous biologically active structures. The utility of the protocol is demonstrated through its application to a brief synthesis of the actin-binding cytotoxin bistramideA.
Total synthesis of bistramide A and its 36(Z) isomers: Differential effect on cell division, differentiation, and apoptosis
Tomas, Loic,Boije Af Gennaes, Gustav,Hiebel, Marie Aude,Hampson, Peter,Gueyrard, David,Pelotier, Beatrice,Yli-Kauhaluoma, Jari,Piva, Olivier,Lord, Janet M.,Goekjian, Peter G.
experimental part, p. 7452 - 7466 (2012/07/28)
The total synthesis of bistramide A and its 36(Z),39(S) and 36(Z),39(R) isomers shows that these compounds have different effects on cell division and apoptosis. The synthesis relies on a novel enol ether-forming reaction for the spiroketal fragment, a kinetic oxa-Michael cyclization reaction for the tetrahydropyran fragment, and an asymmetric crotonylation reaction for the amino acid fragment. Preliminary biological studies show a distinct pattern of influence of each of the three compounds on cell division, differentiation, and apoptosis in HL-60 cells, thus suggesting that these effects are independent activities of the natural product. Copyright
Synthesis of two bioactive natural products: FR252921 and pseudotrienk acid B
Amans, Dominique,Bellosta, Veronique,Cossy, Janine
scheme or table, p. 3457 - 3473 (2009/12/26)
Concise and highly convergent syntheses of the immunosuppressive agent FR252921 and the related antimicrobial natural product pseudotrienic acid B were achieved from a common intermediate by using optically active titanium complexes to control the configuration of the stereogenic centers, a highly stereoand regioselective cross-metathesis to generate the triene moieties, and a Stille cross-coupling to install the dienic units.
Total synthesis of (-)-7-epicylindrospermopsin, a toxic metabolite of the freshwater cyanobacterium Aphanizomenon ovalisporum, and assignment of its absolute configuration
White, James D.,Hansen, Joshua D.
, p. 1963 - 1977 (2007/10/03)
(Chemical Equation Presented) The Z and E nitrones 38 and 39 from condensation of aldehyde 20 with hydroxylamine 36 underwent intramolecular dipolar cycloaddition to give the substituted 1-aza-7-oxobicyclo[2.2.1] heptanes 40 and 41 in a ratio of 2:1, respectively. Reductive N-O bond cleavage of 40 followed by carbonylation gave cyclic urea 47 in which inversion of the secondary alcohol was effected via an oxidation-reduction sequence. After conversion of the p-bromobenzyl ether 50 to azide 54, activation of the cyclic urea as its O-methylisourea and reduction of the azide led to spontaneous cyclization to afford the tricyclic nucleus 59 of cylindrospermopsin. Global deprotection, including hydrolysis of the 2,4-dimethyoxypyrimidine appendage to a uracil, and then monosulfation of the resultant diol 60 afforded a substance identical with natural (-)-7-epicylindrospermopsin (1). The asymmetric synthesis of (-)-7-epicylindrospermopsin defines its absolute configuration as 7S,8R,10S,12S,13R,14S.
Synthesis of bistramide A
Statsuk, Alexander V.,Liu, Dong,Kozmin, Sergey A.
, p. 9546 - 9547 (2007/10/03)
We have developed an efficient and highly stereocontrolled synthesis of bistramide A, a selective activator of protein kinase C isotype δ. Our synthetic strategy featured a novel bidirectional approach for spiroketal construction based on the ring-opening
