Milind D. Sindkhedkar

A NEW ROUTE TO AMINOSUGARS FROM SUGAR NITRONES : SYNTHESIS OF 6-DEOXYNOJIRIMYCIN

Abstract The 1,3-addition of methylmagnesium chloride to dialdose derived nitrones 3 and 7 afforded N- benzylhydroxylamines 4 5 and 8 9 , respectively, in high yields. The stereoselectivity of the addition reaction was improved by the use of trimethylsilyl triflate. The NO bond reductive cleavages of N-benzylhydroxylamines took place in good yields and offered an easy access to N-benzylaminosugars. The potential of these aminosugars is demonstrated by the synthesis of glycosidase inhibitor 6-deoxynojirimycin 1a.

Convenient two-step syntheses of seselin and angelicin derivatives

Abstract Convenient two-step approaches are described for the syntheses of seselin ( 3a ), seselin and angelicin derivatives ( 3b–d and 5a–d ) from 2,4-dihydroxybenzaldehyde ( 1a ) and 2,4-dihydroxyacetophenone ( 1b ) using tandem Claisen rearrangement and Wittig reaction.

An Unusual AlCl3 Catalysed Aromatic Cyclisation Reaction : Novel Synthesis of Tetrahydronaphthoic Acids

An unusual AlCl3 catalysed aromatic cyclisation reaction is described. This is used to develop a novel synthesis of 5,6,7,8-tetrahydro-5-alkyl-1-naphthoic acids (1a–d) from 2-vinylbenzoic acids (3a–d).