1173675-23-4Relevant articles and documents
Stereoselective synthesis of the ABC ring system of norzoanthamine
Ghosh, Subhash,Rivas, Fatima,Fischer, Derek,Gonzalez, Miguel A.,Theodorakis, Emmanuel A.
, p. 941 - 944 (2004)
(Equation presented) An efficient synthesis of enone 4, representing the ABC ring motif of norzoanthamine, is presented. The crucial C22 quaternary center was introduced via a stereoselective methylation of enone 8. The trans-anti-trans relative configura
Enantioselective synthesis of the antiinflammatory agent (-)-acanthoic acid
Ling,Chowdhury,Kramer,Vong,Palladino,Theodorakis
, p. 8843 - 8853 (2007/10/03)
An enantioselective synthesis of the potent antiinflammatory agent (-)-acanthoic acid (1) is described. The successful strategy departs from (-)-Wieland-Miescher ketone (10), which is readily available in both enantiomeric forms and constitutes the starting point toward a fully functionalized AB ring system of 1. Conditions were developed for a regioselective double alkylation at the C4 center of the A ring, which produced compound 32 as a single stereoisomer. Construction of the C ring of 1 was accomplished via a Diels-Alder reaction between sulfur-containing diene 43 and methacrolein (36), which after desulfurization and further functionalization yielded synthetic acanthoic acid. The described synthesis confirms the proposed stereochemistry of the natural product and represents a fully stereocontrolled entry into an underexplored class of biologically active diterpenes.
FACILE SYNTHESIS OF ALKYL 5-ALKOXY-3-OXOPENTANOATES
Sanchez, Ignacio H.,Larraza, Maria Isabel,Brena, Francisco Kuri,Cruz, Adrian,Sotelo, Octavio,Flores, Humberto J.
, p. 299 - 308 (2007/10/02)
A facile synthesis of several alkyl 5-alkoxy-3-oxopentanoates, based on the reductive elimination of triphenylphosphine from the readily available alkyl 5-alkoxy-3-oxo-2-(triphenylphosphoranylidene) pentanoates, is described.
