The diastereoselective approach to enantiomerically pure furyl hydroperoxides of general type 1 has been accomplished starting from (S)-(-)-ethyl lactate. In the first part of the synthesis the alkylating reagents 7a,b were efficiently produced to be used in the second part for a 4-step known methodology to obtain furyl hydroperoxides. The most relevant transformation of the synthesis is the first reported diastereoselective iodoenoletherification of 2-acetyl-4-heptenoate esters 8a,b possessing a phi-chiral center. Furthermore, the final radical oxidation performed on (E)-5-alkylidene-4,5-dihydrofurans 11a,b led to formation of hydroperoxides (S,S)-12a,b in a diastereocontrolled manner due to 1,2-asymmetric induction.
Diastereoselective synthesis of enantiopure 5-[2-(alkoxyalkyl)-1-(hydroperoxypropyl)]-3-alkoxycarbonyl-2-alkyl furans
LATTANZI, Alessandra;SCETTRI, Arrigo
1999
Abstract
The diastereoselective approach to enantiomerically pure furyl hydroperoxides of general type 1 has been accomplished starting from (S)-(-)-ethyl lactate. In the first part of the synthesis the alkylating reagents 7a,b were efficiently produced to be used in the second part for a 4-step known methodology to obtain furyl hydroperoxides. The most relevant transformation of the synthesis is the first reported diastereoselective iodoenoletherification of 2-acetyl-4-heptenoate esters 8a,b possessing a phi-chiral center. Furthermore, the final radical oxidation performed on (E)-5-alkylidene-4,5-dihydrofurans 11a,b led to formation of hydroperoxides (S,S)-12a,b in a diastereocontrolled manner due to 1,2-asymmetric induction.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
