906077-08-5Relevant academic research and scientific papers
A practical one-pot radical-ionic sequence for the preparation of epoxides: Application to the synthesis of unnatural polyhydroxylated alkaloids
Peralta-Hernández, Eduardo,Cortezano-Arellano, Omar,Cordero-Vargas, Alejandro
, p. 6899 - 6902 (2012/02/05)
An efficient one-pot sequence for the preparation of epoxides from α-iodoesters or α-iodonitriles and allylic alcohols is described. This sequence is based on the use of iodine atom transfer reaction onto allylic alcohols followed by a ring closing epoxidation reaction of the halohydrin intermediates. The feasibility of this sequence is showcased in the synthesis of the perhydroaza-azulene, an unnatural analog of castanospermine.
Synthesis of tetrahydroxy perhydroaza-azulenes: Tandem Johnson-Claisen rearrangement of d-glucose-derived allylic alcohols
Markad, Shankar D.,Karanjule, Narayan S.,Sharma, Tarun,Sabharwal, Sushma G.,Puranik, Vedavati G.,Dhavale, Dilip D.
, p. 2549 - 2555 (2008/02/08)
The Johnson-Claisen rearrangement of d-glucose-derived allylic alcohols 5a,b afforded sugar-substituted γ,δ-unsaturated ester 6 in high yield. Conversion of the ester group to an azidomethyl group, epoxidation of the double bond and hydrogenation gave pyr
