Martha Krishnaiah

Stereoselective total synthesis of a potent natural antifungal compound (6S)-5,6,dihydro-6-[(2R)-2-hydroxy-6-phenyl hexyl]-2H-pyran-2-one

A practical stereoselective synthesis of (6S)-5,6,dihydro-6-[(2R)-2-hydroxy-6-phenyl hexyl]-2H-pyran-2-one, a potent natural antifungal compound, is described. The sequence involves diastereoselective iodine-induced electrophilic cyclization, epoxide ring opening with a vinyl Grignard reagent and ring closing metathesis (RCM) as the key steps.

Stereoselective synthesis of bioactive natural spiroacetals aculeatins A and B

The stereoselective synthesis of two naturally occurring bioactive spiroacetals, aculeatins A and B has been accomplished using 1-tetradecanal as the starting material. The sequence introduces diastereoselective iodine-induced electrophilic cyclization and ring opening of epoxide with 1,3-dithiane as the key steps.

An Efficient Stereoselective Total Synthesis of Aculeatins A and B

Aculeatins A and B, two naturally occurring bioactive spiroacetals, have been synthesized efficiently in stereoselective manner starting from 1-tetradecanal. The synthetic strategy involves Maruoka enantioselective allylation, diastereoselective iodine-induced electrophilic cyclization, alkylation of a chiral aldehyde and oxidative spirocyclization as the important steps.

Rapid, efficient and selective conjugate addition of thiols to α, β-unsaturated carbonyl compounds using silica supported sodium hydrogen sulfate under solvent-free conditions†

The conjugate addition of thiols to α, β-unsaturated carbonyl compounds was carried out rapidly (within 2–5 min) and selectively in the presence of silica supported sodium hydrogen sulfate (NaHSO4·SiO2) to form the corresponding Michael adducts in excellent yields (86–95%) at room temperature and under solvent-free conditions. †Part 157 in the series, ‘Studies on novel synthetic methodologies’