62928-74-9Relevant academic research and scientific papers
A stereo- and enantioselective approach to clavulones from tricyclodecadienone using flash vacuum thermolysis
Zhu, Jie,Yang, Ji-Ying,Klunder, Antonius J. H.,Liu, Zhi-Yu,Zwanenburg, Binne
, p. 5847 - 5870 (2007/10/02)
The stereo- and enantioselective synthesis of clavulones 6 and their analogues 48 is described. γ-Hydroxycyclopentenones (-)-13 and 44, which are key intermediates in this approach, are obtained from enantiopure endo-tricyclo[5.2.1.02,6]decadienones (+)-14 and (+)-20 in 6 and 8 steps, respectively. Crucial steps are the reductive epoxy ring opening in compounds (+)-25 and 39 to give the corresponding diols (+)-27 and 40, and the thermal cycloreversion of tricyclodecenones (+)-27 and 41, using the technique of flash vacuum thermolysis (FVT). The synthesis of enantiopure (-)-13 represents a formal total synthesis of clavulones 6. The synthesis of vlavulone analogues (-)-48E and (-)-48Z (X = CH2OH) is completed by condensation of 44 with aldehyde 45 followed by elimination of water and removal of the protective THP-group.
SYNTHESIS AND -CYCLOREVERSION OF CAGE KETONES
Yamashita, Yoshiro,Mukai, Toshio
, p. 1741 - 1744 (2007/10/02)
A series of pentacyclic cage ketones 2b-d having no substituent was synthesized by the photochemical -cycloaddition reaction of corresponding tricyclic dienones 1b-d.The cage ketones 2b-d underwent thermal -cycloreversion to give dienones 1b-d.The reactivities were dependent on the length of the bridge "X".
Photochemical Formation of Strained Cage Compounds and their Acid-catalysed Reversion as a Preliminary Model for Light Energy Conversion
Hamada, Tatsuo,Iijima, Hideo,Yamamoto, Tohru,Numao, Naganori,Hirao, Ken-ichi,Yonemitsu, Osamu
, p. 696 - 697 (2007/10/02)
On irradiation, some Diels-Alder adducts derived from cyclic dienes and dienones gave, quantitatively, strained pentacyclic C12, C11, and C10 cage compounds, which rapidly and completely reverted to the starting compounds with the evolution of heat (18.0-23.5 kcal/mol) when treated with an acid; the C11 system was found to be the most promising for the reversible storage of light energy.
