1228675-53-3Relevant academic research and scientific papers
Synthetic efforts toward the spiroketal core of spirangien a
Guerinot, Amandine,Lepesqueux, Guillaume,Sable, Serge,Reymond, Sebastien,Cossy, Janine
experimental part, p. 5151 - 5163 (2010/10/03)
(Figure presented) Synthetic studies toward the spiroketal core of spirangien A are described. Two synthetic approaches were developed. Both of them use a diastereoselective aldol addition of a lithium enolate derived from a methyl ketone on an aldehyde. In the first approach, the introduction of the (E)-trisubstituted terminal olefin was achieved by using an iron-catalyzed cross-coupling between an alkyl iodide and a vinyl Grignard reagent and a randomly protected spiroketal was obtained. In the second approach, a highly functionalized spiroketal carbamate, which includes 13 stereogenic centers, was successfully isolated.
Polyketide assembly by alkene-alkyne reductive cross-coupling: Spiroketals through the union of homoallylic alcohols
Canterbury, Daniel P.,Micalizio, Glenn C.
supporting information; experimental part, p. 7602 - 7604 (2010/07/08)
A reaction sequence composed of regioselective formal hydroalkynylation, reductive ene-yne cross-coupling, and oxidative cyclization has been developed to prepare stereochemically dense spiroketals. Overall, the chemistry defines a three-component coupling process for the union of two homoallylic alcohol-based substrates with trimethylsilylacetylene.
