102306-78-5Relevant academic research and scientific papers
A concise total synthesis of unprecedented tetranorsesquiterpenoids applanatumol Z5
Wang, Kunkai,Tan, Xiangchuang,Xie, Zhixiang
supporting information, (2020/11/02)
A concise total synthesis of tetranorsesquiterpenoids applanatumol Z5 (3), possessing unique 6/5/5 ring system was disclosed with 7-step in 5-pot from commercially available starting materials. The key elements of the synthesis included an unexpected intramolecular dithiolane with alcohol oxidative coupling/deprotection sequence to create the unsaturated lactone as dienophile and a regioselective Diels-Alder reaction to assemble the 6/5/5 tricyclic scaffold including two vicinal quaternary carbon stereocenters. Late stage the diastereo- and regioselective carbonyl reduction led to achieve the total synthesis of (±) applanatumol Z5 (3).
Synthetic studies of furanosesquiterpenoid tetrahydrolinderazulenes. Total synthesis of (±)-echinofuran
Yim, Ho-Kee,Liao, Yun,Wong, Henry N. C.
, p. 1877 - 1884 (2007/10/03)
Echinofuran (1) was isolated in 1992 and was reported to inhibit cell division of fertilized sea urchin eggs. The synthesis of 1 was achieved by a Ring A→Ring AC→Ring ABC approach employing 3-methyl-4-(trimethylsilyl)furan (2) as a precursor. A Suzuki cou
Preparation, Reactivity, and Spectral Properties of 1,3-Dioxin Vinylogous Esters: Versatile β-Ketovinyl Cation Equivalents
Smith, Amos B.,Dorsey, Bruce D.,Ohba, Masashi,Lupo, Andrew T.,Malamas, Michael S.
, p. 4314 - 4325 (2007/10/02)
A full account of the preparation, reactivity, and spectral properties of three 1,3-dioxin vinylogous esters (4-6) is presented.The synthetic approach of these versatile β-ketovinyl cation equivalents involves a BF3*Et2O-promoted Prins reaction between cyclic 1,3-diketones (i.e., 1,3-cyclopentanedione, 1,3-cyclohexanedione, and 1,3-cycloheptanedione) and either formaldehyde or trioxane.The reactions explored include reductive and alkylative 1,3-ketone transpositions, affording a variety of simple β-unsubstituted and β-substituted α-hydroxymethyl α,β-enones, alkylations with carbon electrophiles, and hydroxylations with oxygen electrophiles.
