528-24-5Relevant articles and documents
Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones
Zimmermann, Nicole,Hilgraf, Robert,Lehmann, Lutz,Ibarra, Daniel,Francke, Wittko
scheme or table, p. 1246 - 1255 (2012/10/08)
Starting from the enantiomers of limonene, all eight stereoisomers of trans-fused dihydronepetalactones were synthesized. Key compounds were pure stereoisomers of 1-acetoxymethyl-2-methyl-5-(2-hydroxy-1-methylethyl)-1- cyclopentene. The stereogenic center of limonene was retained at position 4a of the target compounds and used to stereoselectively control the introduction of the other chiral centers during the synthesis. Basically, this approach could also be used for the synthesis of enantiomerically pure trans-fused iridomyrmecins. Using synthetic reference samples, the combination of enantioselective gas chromatography and mass spectrometry revealed that volatiles released by the endohyperparasitoid wasp Alloxysta victrix contain the enantiomerically pure trans-fused (4R,4aR,7R,7aS)-dihydronepetalactone as a minor component, showing an unusual (R)-configured stereogenic center at position 7.
An efficient synthesis of the Prelog-Djerassi lactone methyl ester from (-)-trans-pulegenic acid
Hacini, Salih,Santelli, Maurice
, p. 7787 - 7792 (2007/10/02)
The (+)-Prelog-Djerassi lactone methyl ester 1 was obtained from trans-pulegenic acid 2 in seven steps in 22 % overall yield; three more steps from an unwanted diastereoisomer gave additionnal 5%.
