Showing papers by "Indrapal Singh Aidhen published in 2010"
TL;DR: In this paper, the synthesis of (+)-varitriol analogues was achieved through the use of Julia olefination and the potential anticancer properties of 1 coupled with their interest in developing building blocks that enable olefin formation under the Julia protocol constitute the basis of their research project.
37 citations
TL;DR: In this article, two simple reactions, N-benzylation and addition of arylmagnesium halide on the WA functionality of the former provided the key intermediate for convenient synthesis of N -phenylsulfonyl protected 4-aryl-1,2,3,4-tetrahydroisoquinoline, through reduction and acid promoted cyclization.
10 citations
TL;DR: In this paper, Weinreb amide functionalities have been synthesized from commercially available o-, m-, and p-toluic acid, enabling efficient C-C bond formation through Wittig reaction with simple and functionalized aldehydes.
8 citations
TL;DR: In this article, a new and convenient synthesis of 2-O-benzyl-3, 4: 5, 6-di-Oisopropylidene-D-glucitol has been accomplished and has been generalized with the syntheses of differently protected Dglucitols at C-2 position.
Abstract: A new and convenient synthesis of 2-O-benzyl-3, 4: 5, 6-di-O-isopropylidene-D-glucitol has been accomplished and has been generalized with the syntheses of differently protected D-glucitols at C-2 position. In the course of our new route to the differently protected D-glucitols at C-2 position, a new D-gluco configured building block, 1-morpholino-(3, 4: 5, 6-di-O-isopropylidene)-D-gluconamide has been achieved.
TL;DR: In this paper, two simple reactions, N-benzylation and addition of arylmagnesium halide on the WA functionality of the former provided the key intermediate for convenient synthesis of N -phenylsulfonyl protected 4-aryl-1,2,3,4-tetrahydroisoquinoline, through reduction and acid promoted cyclization.
Abstract: New synthetic equivalents, N -methoxy- N -methyl- N ′-phenylsulfonyl glycinamide and N -methoxy- N -methyl- N ′-benzyl- N ′- tert -butyloxy carbonyl glycinamide based on WA functionality were developed for the convenient synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinoline framework. Two simple reactions, N-benzylation and addition of arylmagnesium halide on the WA functionality of the former afforded the key intermediate for convenient synthesis of N -phenylsulfonyl protected 4-aryl-1,2,3,4-tetrahydroisoquinoline, through reduction and acid promoted cyclization. With the latter, the addition of arylmagnesium halide on the WA functionality followed by the same protocol afforded the direct synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinolines in good yields. The acid promoted cyclization step enabled concomitant removal of N -Boc protection.
TL;DR: In this paper, the synthesis of (+)-varitriol analogues was achieved through the use of Julia olefination and the potential anticancer properties of 1 coupled with their interest in developing building blocks that enable olefin formation under the Julia protocol constitute the basis of their research project.
Abstract: The synthesis of (+)-varitriol (1) analogues was achieved through the use of Julia olefination. The potential anticancer properties of 1 coupled with our interest in developing building blocks that enable olefin formation under the Julia protocol constitute the basis of our research project. Efforts are aimed at the synthesis of building blocks 2 and 3 and to explore their use towards the synthesis of (+)-varitriol analogues. Herein, we would like to present the synthesis of building block 3 and its ability to react with variety of substituted aromatic-, heterocyclic- and carbohydrate-derived aldehydes to yield alkene 6 in moderate to good yields with E as the major isomer. The successful coupling of 2 with (furanoside moieties) aldehydes 5k, 5m and 5n in particular and the obtainment of compound 23 reflect the promise associated with the new strategy.