292157-65-4Relevant academic research and scientific papers
Total synthesis of (+)-irciniastatin A (a.k.a. psymberin) and (-)-irciniastatin B
An, Chihui,Jurica, Jon A.,Walsh, Shawn P.,Hoye, Adam T.,Smith, Amos B.
, p. 4278 - 4296 (2013/06/27)
A unified synthetic strategy to access (+)-irciniastatin A (a.k.a. psymberin) and (-)-irciniastatin B, two cytotoxic secondary metabolites, has been achieved. Highlights of the convergent strategy comprise a boron-mediated aldol union to set the C(15)-C(17) syn-syn triad, reagent control to set the four stereocenters of the tetrahydropyran core, and a late-stage Curtius rearrangement to install the acid-sensitive stereogenic N,O-aminal. Having achieved the total synthesis of (+)-irciniastatin A, we devised an improved synthetic route to the tetrahydropyran core (13 steps) compared to the first-generation synthesis (22 steps). Construction of the structurally similar (-)-irciniastatin B was then achieved via modification of a late-stage (-)-irciniastatin A intermediate to implement a chemoselective deprotection/oxidation sequence to access the requisite oxidation state at C(11) of the tetrahydropyran core. Of particular significance, the unified strategy will permit late-stage diversification for analogue development, designed to explore the biological role of substitution at the C(11) position of these highly potent tumor cell growth inhibitory molecules.
PEDERIN AND PSYMBERIN AGENTS
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Page/Page column 42-45, (2013/03/26)
Compounds that include a pederin, psymberin or pederin/psymberin chimera scaffold. The pederin scaffold includes a substituent at the C10 and/or C13 position that may include a linker that may be conjugated to a targeting moiety. The psymberin scaffold in
Total synthesis and biological evaluation of pederin, psymberin, and highly potent analogs
Wan, Shuangyi,Wu, Fanghui,Rech, Jason C.,Green, Michael E.,Balachandran, Raghavan,Horne, W. Seth,Day, Billy W.,Floreancig, Paul E.
scheme or table, p. 16668 - 16679 (2011/12/14)
The potent cytotoxins pederin and psymberin have been prepared through concise synthetic routes (10 and 14 steps in the longest linear sequences, respectively) that proceed via a late-stage multicomponent approach to construct the N-acyl aminal linkages.
Total synthesis of (+)-psymberin (irciniastatin A): Catalytic reagent control as the strategic cornerstone
Smith III, Amos B.,Jurica, Jon A.,Walsh, Shawn P.
scheme or table, p. 5625 - 5628 (2009/06/18)
(Chemical Equation Presented) An effective total synthesis of the marine sponge cytotoxin (+)-psymberin [irciniastatin A (1)] has been achieved. Highlights of the strategy include a Diels-Alder reaction between a bis-siloxy diene and an allene to construct the aromatic ring, a boron-mediated aldol reaction to elaborate the C(15-17) all syn stereotriad, catalytic reagent control to set the C(8, 9,11 and 13) stereogenic centers of the tetrahydropyran core, and a late-stage Curtius rearrangement to install the sensitive N,0-aminal moiety. The synthesis proceeds with a longest linear sequence of 21 steps from commercially available 2,2-dimethyl-1,3-propanediol.
Synthesis of 4-hydroxy- and 2,4-dihydroxy-homophthalates by [4+2] cycloaddition of 1,3-bis(silyloxy)-1,3-butadienes with dimethyl allene-1,3-dicarboxylate
Hussain, Ibrar,Yawer, Mirza A.,Appel, Bettina,Sher, Muhammad,Mahal, Ahmed,Villinger, Alexander,Fischer, Christine,Langer, Peter
, p. 8003 - 8009 (2008/12/20)
The reaction of 1,3-bis(trimethylsiloxy)-1,3-butadienes with dimethyl allene-1,3-dicarboxylate provides a convenient and regioselective approach to a variety of functionalized 4-hydroxy- and 2,4-dihydroxy-homophthalates.
Concise and stereoselective synthesis of the N7-C25 fragment of psymberin
Rech, Jason C.,Floreancig, Paul E.
, p. 5175 - 5178 (2007/10/03)
(Chemical Equation Presented) The N7-C25 fragment of the potent and selective cytotoxic agent psymberin has been prepared through a short (12 linear steps, 15 total steps) and stereoselective sequence. Highlights of this route includ
