195871-32-0Relevant articles and documents
New methods for the synthesis of naphthyl amines; Application to the synthesis of dihydrosanguinarine, sanguinarine, oxysanguinarine and (±)-maclekarpines B and C
Tatton, Matthew R.,Simpson, Iain,Donohoe, Timothy J.
, p. 11314 - 11316 (2014/11/07)
A new method for preparing naphthyl amines from 1,5 unsaturated dicarbonyl precursors is described; the utility of this new method was proven in the syntheses of several natural products, all containing the benzo[c]phenanthridine core and enabled by a radical promoted cyclisation of the naphthyl amine products formed in the key cyclisation. the Partner Organisations 2014.
Design and synthesis of chiral and racemic phosphonate-based haptens for the induction of aldolase catalytic antibodies
Mu, YongQi,Gibbs, Richard A.
, p. 1327 - 1337 (2007/10/03)
A novel strategy for the generation of aldolase catalytic antibodies, based on the use of antibody-catalyzed enol ester hydrolysis as a 'trigger' to generate a reactive enolate intermediate, is described. A model system to test this strategy was developed and substrate 8 was synthesized. However, the targeted bifunctional haptens 11 and 33 were synthetically inaccessible, and therefore the alternative phosphonate hapten 39 was prepared. The key step in the synthesis of 39 was the direct generation of an unprotected phosphonate precursor via coupling of the secondary alcohol 37 with CH3P(O)CI2. The chiral counterpart of hapten 39 was also synthesized from alcohol 46, prepared by Corey's asymmetric reduction method. One polyclonal antibody preparation generated from 39 appeared to catalyze the hydrolysis of the secondary acetate 49, but not the desired aldol cyclization of 8. Possible rationales for this finding are discussed.
Asymmetric Synthesis of 4,4-Disubstituted 1-Naphthalenones. Diastereoselectivity as a Function of Metal Oxides
Wuensch, Thomas,Meyers, A. I.
, p. 4233 - 4235 (2007/10/02)
Chiral tricyclic lactam (5) was sequentionally metalated (LDA or LDA/zirconocene halides) and alkylated to give quaternary alkylation products (8) in 6-54:1 diastereomeric ratio.Reduction and hydrolysis furnish the title compound in three steps with >99 p