5406-18-8Relevant articles and documents
Highly Stereoselective Synthesis of Fused Tetrahydropyrans via Lewis-Acid-Promoted Double C(sp3)-H Bond Functionalization
Yokoo, Kazuma,Sakai, Dan,Mori, Keiji
, p. 5801 - 5805 (2020)
We have achieved a sequential hydride-shift-triggered double C(sp3)-H bond functionalization at a position adjacent to an oxygen atom and a benzylic/aliphatic position through the employment of substrates with a dialkyl group in the alkyl chain, which enabled the highly diastereoselective synthesis of fused tetrahydropyrans.
Catalytic δ-hydroxyalkynone rearrangement in the stereoselective total synthesis of centrolobine, engelheptanoxides A and C and analogues
Ahmad, Mohammad N.,Chopra, Sidharth,Fernandes, Rodney A.,Kumar, Praveen
, (2021/08/13)
A catalytic stereoselective total synthesis of centrolobine and engelheptanoxides A and C has been completed via a metal-free catalytic δ-hydroxyalkynone rearrangement to 2,3-dihydro-4H-pyran-4-one and diastereoselective hydrogenation to the all syn-2,4,6-trisubstituted pyran strategy. The onliest required chirality was introduced by Jacobsen kinetic resolution, which further directed the diastereoselective hydrogenation. A first stereoselective synthesis of engelheptanoxide A is also accomplished. The analogues and derivatives of centrolobine and engelheptanoxides prepared were evaluated for antitubercular activity against M. tuberculosis H37Rv ATCC 27294.
Synthetic and Mechanistic Studies on 2,3-Dihydrobenzo[ b ][1,4]-oxaselenines Formation from Selenocyanates
Bonesi, Sergio M.,Cattaneo, Mauricio,Chao, María N.,Rodriguez, Juan B.,Sanchez Gonzalez, Jonathan,Szajnman, Sergio H.
, p. 1643 - 1658 (2020/05/25)
An expedient preparation of selenium-containing hetero-cycles via an m -chloroperbenzoic acid-mediated seleno-annulation starting from selenocyanate derivatives is described. In spite of its significance, this cyclization reaction is virtually understudied not only from the point of view of its scope, but also from the mechanistic aspects associated to this remarkable transformation. In this sense, several selenocyanate and thiocyanate derivatives bearing an aromatic ring were evaluated as substrates under different reaction conditions of this interesting cyclization yielding important insights on its scope as well as relevant information on the reaction mechanism.
