288580-72-3Relevant academic research and scientific papers
A formal total synthesis of (-)-brevisamide, a marine monocyclic ether amide
Lee, Jungmee,Oh, Hong-Se,Kang, Han-Young
supporting information, p. 1099 - 1102 (2015/02/19)
A formal total synthesis of (-)-brevisamide, a monocyclic ether amide with architecturally unique structural features, has been achieved. The tetrahydropyran core part of the target was synthesized by the aldol reaction followed by ring-closing metathesis using the Grubbs second generation catalyst. After the stereochemistry at the carbon center bearing the hydroxy group was adjusted, the carbon-carbon double bond was stereoselectively reduced by catalytic hydrogenation. Finally, introduction of the amino group was followed by acetylation, which provided the desired advanced intermediate.
The stereoselective total synthesis of (+)-stagonolide B
Srihari, Pabbaraja,Kumaraswamy, Boyapelly,Somaiah, Ragam,Yadav, Jhillu S.
scheme or table, p. 1039 - 1045 (2010/04/29)
The stereoselective total synthesis of the nonenolide, (+)-stagonolide B is described. The key steps involve epoxide homologation, hydrolytic kinetic resolution and ring-closing metathesis.
1,8-Diazabicyclo[5.4.0]undec-7-ene: A remarkable base in the debromination of 4- or 5-substituted N-benzyl α-bromo-α-p- toluenesulfonylglutarimide
Chang, Meng-Yang,Lin, John Yi-Chung,Chen, Shui-Tein,Chang, Nein-Chen
, p. 1015 - 1024 (2007/10/03)
Debromination of N-benzyl 4- or 5-substituted α-bromo-α-p- toluenesulfonylglutarimides is achieved with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to give the N-benzyl 4- or 5-substituted α-p- toluenesulfonylglutarimides. The DBU/THF system is applied to a new methodology for the synthesis of bicyclic glutarimide skeleton in moderate yields.
