1217182-52-9Relevant academic research and scientific papers
A gold-catalyzed alkyne-diol cycloisomerization for the synthesis of oxygenated 5,5-spiroketals
Tlais, Sami F.,Dudley, Gregory B.
, p. 570 - 577 (2011)
A highly efficient synthesis of oxygenated 5,5-spiroketals was performed towards the synthesis of the cephalosporolides. Gold(I) chloride in methanol induced the cycloisomerization of a protected alkyne triol with concomitant deprotection to give a strate
Stereocontrol of 5,5-spiroketals in the synthesis of cephalosporolide H epimers
Tlais, Sami F.,Dudley, Gregory B.
supporting information; experimental part, p. 4698 - 4701 (2011/01/12)
A blueprint for controlling the stereochemistry of oxygenated 5,5-spiroketals using chelation effects is provided. Chelation specifically of zinc salts (other protic and Lewis acids were less effective) between the spiroketal oxygen and an appropriately positioned alcohol group overrides normal biases in the preparation of 5,5-spiroketals, as illustrated by the stereocontrolled synthesis of epimeric cephalosporolide H isomers. This study provides new and valuable information for prescribing the chirality of the stereogenic core of 5,5-spiroketals.
A striking exception to the chelate model for acyclic diastereocontrol: Efficient access to a versatile propargyl alcohol for chemical synthesis
Tlais, Sami F.,Clark, Ronald J.,Dudley, Gregory B.
experimental part, p. 5216 - 5222 (2010/03/30)
The four-step, asymmetric synthesis of a chiral propargyl alcohol 1 from (R)-pantolactone is described. A key feature of the synthesis is a diastereoselective acetylide addition to a chiral α-alkoxy-aldehyde 7, in which unusual Felkin selectivity is obser
