85379-16-4Relevant academic research and scientific papers
Synthesis of conjugated γ- and δ-lactones from aldehydes and ketones via a vinylation(allylation)-ring closing metathesis-oxidation sequence
Marco, J. Alberto,Carda, Miguel,Rodríguez, Santiago,Castillo, Encarnación,Kneeteman, María N.
, p. 4085 - 4101 (2007/10/03)
Nucleophilic C-vinylation and C-allylation of aldehydes and ketones followed by O-allylation of the obtained carbinols gave the corresponding allyl or homoallyl ethers, respectively. Ring-closing metathesis of these compounds afforded in many cases cyclic ethers (dihydrofurans and dihydropyrans, respectively) bearing disubstituted and trisubstituted C=C bonds. These were then subjected to allylic oxidation to yield conjugated γ- and δ-lactones. Reasons for the observed failures are presented and discussed.
Synthesis of conjugated γ- and δ-lactones from aldehydes and ketones via a vinylation/allylation-ring closing metathesis-oxidation sequence
Carda, Miguel,Castillo, Encarnación,Rodríguez, Santiago,Uriel, Santiago,Marco, J. Alberto
, p. 1639 - 1641 (2007/10/03)
Nucleophilic C-vinylation or C-allylation of aldehydes and ketones followed by O-allylation of the obtained carbinols gave the corresponding allyl ethers. Ring-closing metathesis of the latter afforded cyclic ethers (dihydrofurans and dihydropyrans, respectively) which were then subjected to allylic oxidation to yield conjugated γ- and δ-lactones.
A short synthesis of naturally occurring and other analogues of plakinic acids that contain the 1,2-dioxolane group
Bloodworth,Bothwell, Brian D.,Collins, Andrew N.,Maidwell, Nicola L.
, p. 1885 - 1888 (2007/10/03)
Natural and unnatural analogues 4 of plakinic acids A, C and D have been prepared in three steps from alkan-2-ones by (i) LDA-induced condensation with ethyl-3-methylbut-2-enoate to give (2Z)-3,5-dimethylalka-2,4-dienoic acids 10, then (ii) isomerisation to the 2E-isomers 5 and finally (iii) peroxymercuriation with 30% hydrogen peroxide and reduction in situ with sodium borohydride.
