The prevalence of solvent effects in heterogeneous catalysis in condensed media has motivated developing quantitative kinetic, and theoretical assessments of solvent structures and their interactions with reaction intermediates and transition states. 18422-53-2, Name is 1,2:4,5-Di-O-Isopropylidene-Beta-D-Erythro-2,3-Hexodiulo-2,6-Pyranose, SMILES is O=C1[C@@]2(OC[C@]3([H])[C@@]1([H])OC(C)(O3)C)OC(C)(OC2)C, in an article , author is Padwa, A, once mentioned of 18422-53-2, Category: dioxoles.
The total syntheses of gamma -lycorane and (+/-)-1-deoxylycorine were accomplished using an intramolecular Diels-Alder cycloaddition of a furanyl carbamate as the key step. The initially formed [4+2]-cycloadduct undergoes nitrogen assisted ring opening followed by deprotonatian/reprotonation of the resulting zwitterion to give a rearranged hexahydroindolinone. The stereochemical outcome of the IMDAF cycloaddition has the side arm of the tethered alkenyl group oriented syn with respect to the oxygen bridge. The key intermediate used in both syntheses corresponds to hexahydroindolinone 20. Removal of the t-Boc group in 20 followed by reaction with 6-iodobenzo[1,3] dioxole-5-carbonyl chloride afforded enamide 22. Treatment of this compound with Pd(OAc)(2) employing the Jeffrey modification of the Heck reaction provided the galantfhan tetracycle 24 in good yield. Compound 24 was subsequently converted into (+/-)-gamma -lycorane using a four-step procedure to establish the cis-B, C-ring junction. A radical-based cyclization of the related enamide 33 was used for the synthesis of 1-deoxylycorine. Heating a benzene solution of 33 with AIBN and n-Bu3SnH at reflux gave the tetracyclic compound 38 possessing the requisite trans fusion between rings B and C in good yield. After hydrolysis and oxidation of 38 to 40, an oxidative decarboxylation reaction was used to provide the C-2-C-3-C-12 allylic alcohol unit characteristic of the lycorine alkaloids The resulting enone was eventually transformed into (+/-)-1-deoxylycorine via known synthetic intermediates.
But sometimes, even after several years of basic chemistry education, it is not easy to form a clear picture on how they govern reactivity! 18422-53-2, you can contact me at any time and look forward to more communication. Category: dioxoles.
Reference:
1,3-Benzodioxole – Wikipedia,
,Dioxole | C3H4O2 – PubChem