2259-07-6Relevant articles and documents
Friedelane triterpenoids: Transformations toward A-ring modifications including 2-: Homo derivatives
Das, Jayanta,Sarkar, Antara,Ghosh, Pranab
, p. 6673 - 6688 (2018/05/07)
Friedelin and its derivatives, commonly known as friedelane triterpenoids, exhibit potential biological effects ranging from antimicrobial to anticancer to anti-HIV. To modify the A-ring of the pentacyclic triterpenoid, various transformative scopes have been utilized. Herein, some simple unprecedented transformative protocols have been accomplished towards furnishing 42 (25 new) A-ring modified pentacyclic friedelane triterpenoids. It is worth noting that the modifications include the all-new 2-homo derivatives. The one-pot BF3·OEt2-mediated oxidative transformation of friedelin to yield friedel-3-enol acetate as the major product was one of the key reactions. A group of isomeric A-ring modifications was produced on the basis of simple transformations on suitable friedelane-based molecules. The syntheses of the novel 2-homofriedelanes were envisioned from the transformative reactions of the designed triterpenoid 3-chlorofriedel-2-ene-2-carbaldehyde, which was isolated as the major product from the reaction of friedelin with the novel Vilsmeier-Haack reagent. New A-ring modified derivatives were also obtained due to further interesting transformations of 3-chlorofriedel-3-ene, isolated as side products from the same reaction. Again, considering the scope of the 3-chloro-2-enal moiety associated with the A-ring of the triterpenoid, some heterocycle-linked- (bonded to C3) 2-homofriedelane triterpenoids were synthesized. Various common reaction strategies were employed on suitable substrates to finally achieve a series of C2,C3-; C3,C4- and C2,C3,C4-functionalized as well as 2-homofriedelane triterpenoids with just one to four efficient steps.
Synthesis of saponins with cholestanol, cholesterol, and friedelanol as aglycones
Schimmel, Joerg,Eleuterio, M. Ines Passos,Ritter, Gerd,Schmidt, Richard R.
, p. 1701 - 1721 (2007/10/03)
Procedures for the synthesis of branched Xylss(1→3)[Galss- (1→2)]-Glc and Xylss(1→3)[Galss(1→2)]-GlcUA trisaccharides ss-linked to the 3-O of cholesterol, cholestanol, and friedelanol, respectively, were developed. To this end, ss-selective glucosylation
REDUCTION OF KETONES TO EPIMERIC ALCOHOLS WITH POTASSIUM HYDROXIDE-DIETHYLENE GLYCOL
Pradhan, B. P.,Hassan, A.,Ray, T.
, p. 2513 - 2516 (2007/10/02)
Triterpenoid ketones have been reduced to epimeric alcohols on boiling with potassium hydroxide in diethylene glycol. α,β-unsaturated ketone furnished saturated epimeric alcohols.
Carbon-13 Resonance Assignments of some Friedelanes and Taraxasteranes
Patra, Amarendra,Mukhopadhyay, Apurba K.,Mitra, Alok K.
, p. 166 - 168 (2007/10/02)
Carbon-13 signal assignments of taraxasteryl acetate, taraxasteryl palmitate, taraxasterol and epi-friedenyl acetate are reported.Some signal assignments of the friedelanones, reported recently by others, are inconsistent and require revision.
