80361-30-4Relevant academic research and scientific papers
A Synthesis of (±)-Aplydactone
Meier, Robin,Trauner, Dirk
supporting information, p. 11251 - 11255 (2016/10/13)
Aplydactone is an unusual brominated sesquiterpenoid isolated from the sea hare Aplysia dactylomela. Its highly strained skeleton contains two four- and three six-membered rings and features three adjacent quaternary carbon atoms. Although it is most likely of photochemical origin, attempts to generate it from a chamigrane precursor have failed thus far. In this work, we present a total synthesis of aplydactone that relies on two photochemical key steps that are not biomimetic but highly effective in establishing the two cyclobutane rings. Our synthesis also features an unusual Barbier-type cyclization and culminates in new radical conditions to install the sterically hindered secondary bromide of the natural product.
Ethyl glyoxylate N -tosylhydrazone as sulfonyl-transfer reagent in base-catalyzed sulfa-Michael reactions
Fernandez, Maitane,Uria, Uxue,Orbe, Lucia,Vicario, Jose L.,Reyes, Efraim,Carrillo, Luisa
, p. 441 - 445 (2014/01/17)
Ethyl glyoxylate N-tosylhydrazone has been identified as an excellent sulfonyl anion surrogate in the DBU-catalyzed conjugate addition reaction with enones and enals for the synthesis of functionalized sulfones. The reaction proceeds under base-catalyzed conditions and provides a direct access to γ-keto- and γ-hydroxy sulfones in a simple and reliable way through a sulfa-Michael reaction that proceeds with high yield and chemoselectivity.
FeCl3ATMSCl: An effective catalytic system for the conjugate addition of sodium p-toluenesulfinate to αβ-enones
Sreedhar,Reddy, M. Amamath,Reddy, P. Surendra
experimental part, p. 1949 - 1952 (2009/04/10)
A new protocol for the β-sulfonation of αβ-unsaturated carbonyl compounds is described. The method employs FeCl3 as catalyst and TMSC1 as additive for conjugate addition of sodiump-toluenesulfinate to enones.
Synthesis of cis-Jasmone via the Retroaldol-aldol Condensation of 3-(cis-3-hexenyl)-2-cyclopentenone in an Autoclave
Yoshida, Takashi,Saito, Shojiro
, p. 3931 - 3932 (2007/10/02)
cis-Jasmone was efficiently synthesized from 2-cyclopentenone.The treatment of cyclopentenone with sodium p-toluenesulfinate gave 3-(p-tolylsulfonyl)cyclopentanone in a 92.5percent yield.The alkylation of the sulfone, after the protection of the ketone, with cis-1-bromo-3-hexene, followed by desulfonylation with 5percent hydrochloric acid in tetrahydrofuran, afforded 3-(cis-3-hexenyl)-2-cyclopentenone in a good yield.The retroaldol-aldol condensation of the cyclopentenone in a stainless steel autoclave in presence of 5percent sodium hydroxide yielded cis-jasmone in a 80percent yield.
