67903-06-4Relevant academic research and scientific papers
Studies on photochemical rearrangement of non-oxygenated bicyclo[2.2.2]octenones and mono-oxygenated bicyclo[2.2.2]octenones from masked o-benzoquinones: Access to protoilludane and marasmane skeletons
Hung, Wei-Chun,Chen, Yung-Ching,Niu, Guang-Hao,Chuang, Gary J.
, p. 383 - 398 (2020)
In this work, we described flexible approaches to protoilludane-like (5,6,4-tricyclic ring) and marasmane-like (5,6,3-tricyclic ring) skeletons with naturally occurring cis/anti/cis stereochemistry using photochemical rearrangement of bicyclo[2.2.2]octeno
Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents
Shimizu, Hisato,Yoshimura, Akira,Noguchi, Keiichi,Nemykin, Victor N.,Zhdankin, Viktor V.,Saito, Akio
supporting information, p. 531 - 536 (2018/03/21)
[Bis(trifluoroacetoxy)iodo]benzene (BTI) and (diacetoxyiodo)benzene (DIB) efficiently promote the formation of acylnitroso species from hydroxamic acids in the presence of various dienes to give the corresponding hetero-Diels-Alder (HDA) adducts in moderate to high yields. The present method could be applied to the HDA reactions of acylnitroso species with o-benzoquinones generated by the oxidative dearomatization of guaiacols.
Photoinduced Decarbonylative Rearrangement of Bicyclo[2.2.2]Octenones: Synthesis of the Marasmane Skeleton
Wang, Chun-Chieh,Ku, Yi-Chen,Chuang, Gary Jing
, p. 10979 - 10991 (2015/11/18)
The marasmane sesquiterpenoid structure can be found in the skeleton of a variety of natural products bearing interesting bioactivity. The unique fused-5,6,3-tricyclic ring structure, in which the rings are cis-fused and the five- and three-membered rings are mutually trans, provides a synthetic challenge for organic chemists. In this work, we took advantage of the photoinduced decarbonylative rearrangement of bicyclo[2.2.2]octenone to develop a new methodology for construction of the highly functionalized fused-5,6,3-tricyclic ring structure in a concise reaction sequence.
The hetero Diels-Alder reactions of masked o-benzoquinones with nitroso compounds
Lin,Liao
, p. 1624 - 1625 (2007/10/03)
The first examples of hetero Diels-Alder reaction of masked o-benzoquinones with nitroso dienophiles leading to novel and highly functionalized heterocycles, which are potential intermediates for nitrogenous natural products are reported.
