Synthese von (±)4′-γ,γ-dimethylallyl-naringenin (selinon)

N-Methoxy-N-acylnitrenium Ions: Application to the Formal Synthesis of (−)-TAN1251A

“…Having prepared the 1,4-diazabicyclo[3.2.1]octanone core of 7 in 13 steps, we now proceeded to install the benzyl side chain. Accordingly, generation of the enolate of 9 with LDA in THF and subsequent trapping with p -prenyloxybenzaldehyde ( 17 ) (2 equiv) gave a 1.2:1 mixture of aldol products in a combined yield of 80%, as reported by Kawahara (Scheme ) . Rather than separate this mixture, we found that reaction with MsCl/Et 3 N and elimination of the resulting mixture of mesylates with t BuOK gave α,β-unsaturated amide 19 as a single stereoisomer in 75% overall yield.…”

Synthesis and Biological Evaluation of (±)-Abyssinone II and Its Analogues as Aromatase Inhibitors for Chemoprevention of Breast Cancer

“…However, the MOM and methoxy ethers were stable under the reaction conditions and prenylation occurred in very high yield. Aldehydes 5g 34 and 5h 35 were also synthesized in excellent yield, as shown in Scheme 4.…”

Prenylated flavanones and flavanonols as chemical markers in Glycosmis species (Rutaceae)

“…After isolation and identification they all turned out to be derivatives of flavanones and flavanonols basically falling into two groups by different modes of prenylation. O-Prenylation at position C-4 0 was shown to be widespread in G. chlorosperma represented by the two already known derivatives selinone (1) and 7-O-methylselinone (2) (Seshadri and Sood, 1967;Chari et al, 1970;Ahsan et al, 1994). Independently from taxonomic segregations into different varieties the HPLC profiles of the collections mentioned above showed significant differences in accumulating selinones 1 and/or 2 often vicarious with co-occurring sulphur-containing amides (Vajrodaya, 1998;Lukaseder, 2000;Hehenberger, 2007).…”