New chiral auxiliaries from waste paper

SAROTTI, A.M.; SPANEVELLO, R.A.; SUÁREZ, A.G.

CANELA, BRASIL

Congreso; 11th Brazilian Meeting on Organic Synthesis; 2005

The potential for obtaining useful chemicals from cellulosic waste materials have been investigated through the pyrolysis of acid-pretreated waste paper. Levoglucosenone (1) (1,6-anhydro-3,4-dideoxy-b-D-glycero-hex-3-enopyranos-2-ulose), a bicyclic enone, is the major product of the pyrolysis of cellulose or cellulose-containing materials. During the last decade this versatile and readily available member of the carbohydrate derived chiral pool, has been intensively used as chiral synthon in the synthesis of a wide variety of natural and unnatural products, some of them showing interesting biological activities. Our interest in this field is focused on the potential use of this chiral building block in the synthesis of asymmetric inductors.