(3-KETOTETRAHYDROFURAN-2-YL)ETHANAL DERIVATIVES AND A METHOD FOR THEIR PREPARATION

摘要

Compounds having utility in medicine in countering cellular malfunction e.g. in conditions embraced by the general term "cancer", which compounds normally exist as a keto-enol tautomeric pair, the racemic keto form of which is represented by formula (Ia), wherein R is a hydrogen, lower alkyl, acyl, or another functional group of up to 6 carbons including at least one hetero atom, which atom may be directly bonded to the beta -carbon, which compound may be in the acyclic form shown or in a cyclic form as equilibrium keto-enol tautomer derivatives and anomeric forms thereof, including enantiomers when R is hydrogen and diastereoisomers when R is another group. A method of obtaining such a compound comprises selecting an appropriate dihydrofuran having a protected primary alcohol side chain in the 2-position, subjecting the said protected alcohol side chain-substituted dihydrofuran to oxidation using a chromium-based reagent to yield the corresponding acid, subjecting said acid to iodolactonisation conditions to yield the cis,cis,trans-trisubstituted iodo-lactone which upon displacement of the iodine provides the cis,cis,cis-tri-substituted hydroxylactone which is capable of being reduced to obtain a lactol which is in equilibrium with the corresponding open chain aldehyde.