60014-80-4Relevant academic research and scientific papers
An approach toward the total synthesis of subergorgic acid
Gilbert, John C.,Yin, Jiandong
, p. 5482 - 5490 (2008/12/20)
Ireland-Claisen rearrangement of a substituted alkenyl cyclopentanecarboxylate provided a monocyclic isomer containing the proper stereochemistry for four of the five stereogenic centers in subergorgic acid. Efforts to construct the additional rings in the molecule were thwarted as a result of steric and other factors. The results provide insights regarding the Ireland-Claisen rearrangement in five-membered ring systems. The formation of spiro-compounds from sterically and stereoelectronically demanding systems as reported herein has the potential to serve as a general strategy for the synthesis of such sub-units in both natural and unnatural products.
Synthesis of trisubstituted and tetrasubstituted alkenes via a manganate-induced migration-elimination process
Kakiya, Hirotada,Shinokubo, Hiroshi,Oshima, Koichiro
, p. 10063 - 10069 (2007/10/03)
Preparation of alkenes via a manganate-induced alkylation-elimination sequence was investigated. The reaction of 2-alkoxy-1,1-dibromoalkanes with trialkylmanganates afforded disubstituted or trisubstituted alkenes. Treatment of 2-alkoxy-1,1,1-tribromoalkanes with trialkylmanganates provided trisubstituted or tetrasubstituted alkenes through bromine-metal exchange, transfer of two alkyl groups from manganese to carbon, and successive elimination of metal and the β-alkoxy moieties.
Synthesis of Mono and gem-Dihalogeno-olefins from Carbonyl Compounds and in situ Generated Lithium Carbenoids
Barluenga, Jose,Fernandez-Simon, Jose L.,Concellon, Jose M.,Yus, Miguel
, p. 691 - 694 (2007/10/02)
The treatment of carbonyl compounds (5) with dihalogenomethane and lithium dicyclohexylamide at -78 deg C leads after acid hydrolysis to the crude alcohols (6), which by silylation with trimethylchlorosilane-hexamethyldisilazane-pyridine affords the crude
