Synthesis of new chiral heterocycles from fenchone and menthone.

BROUSSE BEATRIZ N.; MARTINS ALHO MIRIAM A; MOGLIONI ALBERTINA G.; MOLTRASIO GRACIELA Y.; D'ACCORSO NORMA B.

Çuritiba - Brasil

Congreso; IX Brazilian Meeting on Organic Synthesis; 2001

Sociedad Brasilera de Química

Recently we have informed about the preparation of several tiadiazolines by cyclation of the corresponding tiosemicarbazones.1 These tiadiazolines are of interest from the viewpoint of their use as potential pharmaceutical drugs Among the different types of chiral natural products, terpenes have received the less study, in spite of enantiomeric purity of some of them and their accessibility. The tiosemicarbazones of terpenes could be the starting material for synthesis of chiral tiadiazolines. In this work we report the preparation of chiral tiadiazolines starting from two natural monoterpenes, the fenchone and the mentone. Stereochemical assignment of the compounds synthesizes is made by NMR spectroscopy and XRay analyses.1 These tiadiazolines are of interest from the viewpoint of their use as potential pharmaceutical drugs Among the different types of chiral natural products, terpenes have received the less study, in spite of enantiomeric purity of some of them and their accessibility. The tiosemicarbazones of terpenes could be the starting material for synthesis of chiral tiadiazolines. In this work we report the preparation of chiral tiadiazolines starting from two natural monoterpenes, the fenchone and the mentone. Stereochemical assignment of the compounds synthesizes is made by NMR spectroscopy and XRay analyses.