62421-33-4Relevant articles and documents
Stereodefined N,O-acetals: Pd-catalyzed synthesis from homopropargylic amines and utility in the flexible synthesis of 2,6-substituted piperidines
Kim, Haejin,Rhee, Young Ho
supporting information; scheme or table, p. 4011 - 4014 (2012/04/10)
We developed a conceptually new synthetic strategy which exploits the stereochemical information of labile acyclic N,O-acetals. The key to this strategy, chemo- and stereoselective synthesis of N,O-acetals, was achieved by the Pd-catalyzed addition of sulfonyl-protected homopropargylic amines to alkoxyallene. The N,O-acetals generated in this way were combined with Au-catalyzed cycloisomerization to give an access to 2,6-disubstituted piperidines with stereochemical flexibility.
Absolute configuration of insect-produced epilachnene
Farmer, Jay J.,Attygalle, Athula B.,Smedley, Scott R.,Eisner, Thomas,Meinwald, Jerrold
, p. 2787 - 2790 (2007/10/03)
Samples of (X) and (S)-epilachnene [(5Z)-11-propyl-12-azacyclotetradec-5-en olide] were synthesized from (R) and (S)-norvaline. The diastereomeric α-methoxy-α-trifluoromethylphenylacetyl amides of these synthetic samples, prepared using (S) α-methoxy-α-trifluoromethylphenylacetyl chloride, were well resolved by gas chromatography. Analogous derivatization and gas chromatographic analysis of a sample of epilachnene from the pupal secretion of the coccinellid beetle, Epilachna varivestis, established that the natural product is (S)-epilachnene.