94235-22-0Relevant academic research and scientific papers
IBX as a catalyst for dehydration of hydroperoxides: Green entry to α,β-unsaturated ketones: Via oxygenative allylic transposition
Kuga, Tetsuya,Sasano, Yusuke,Iwabuchi, Yoshiharu
, p. 798 - 801 (2018)
A catalytic transformation of allylic hydroperoxides into α,β-unsaturated carbonyl compounds using IBX as a dehydration catalyst is described. The combination of a singlet oxygen ene reaction and the IBX-catalyzed dehydration provides α,β-unsaturated carbonyl compounds from alkenes via oxygenative allylic transposition with H2O as the only byproduct.
Synthesis of pluraflavin A "aglycone"
Wright, Benjamin J. D.,Hartung, John,Peng, Feng,Van De Water, Ryan,Liu, Haibo,Tan, Quen-Hui,Chou, Ting-Chao,Danishefsky, Samuel J.
supporting information; experimental part, p. 16786 - 16790 (2009/04/14)
The "aglycone" of pluraflavin A (2) has been synthesized. The key features of this synthesis include a 1,3-dipolar cycloaddition between a nitrile oxide (cf. 14) and an olefin (22) to yield an isoxazoline followed by subsequent conversion into the γ-pyrone of pluraflavin A. The epoxide moiety linked to the pyrone is installed prior to Diels-Alder installation of the D ring, which allows access to a number of potentially active cytotoxic intermediates en route to the final compound. The preliminary in vitro results of two such compounds are also included with the racemic title compound exhibiting cytotoxicity in the nanomolar range.
Photochemical preparation of cyclopropanes from cyclobutanones
Ramnauth,Lee-Ruff
, p. 114 - 120 (2007/10/03)
A general method for the preparation of cyclopropanes is reported. Triplet-photosensitized reactions of a series of cyclobutanones give cyclopropanes as the major product. Part 1 describes the synthesis of substituted cyclobutanones used in this study. In Part 2, the photo-reactions of cyclobutanones are reported. Triplet-sensitized reactions of cyclobutanones using acetone as a sensitizer give cyclopropanes as the major non-polar products. The extent of photodecarbonylation seems to be dependent on α-substitution. Electron-donating groups promote decarbonylation while electron-withdrawing groups favour cycloelimination.
A NEW SYNTHESIS OF ALLYLIC ALCOHOLS OR THEIR DERIVATIVES VIA REDUCTIVE ELIMINATION FROM γ-PHENYLTHIO-β-NITROALCOHOLS WITH TRIBUTYLTINHIDRIDE
Ono, Noboru,Kamimura, Akio,Kaji, Aritsune
, p. 5319 - 5322 (2007/10/02)
Allylic alcohols are readily prepared by the Bu3SnH-promoted elimination reaction from γ-phenylthio-β-nitroalcohols which are obtained by the joint reaayction of nitroolefins, thiophenol, and aldehydes.
