G. Satheesh

Synthesis of (+)-lycoricidine by the application of oxidative and regioselective ring-opening of aziridines.

A highly stereoselective total synthesis of (+)-lycoricidine has been described. The salient features of this synthesis are the one-pot elimination followed by allylation reaction, ring-closing metathesis, stereoselective aziridine formation, Dess-Martin periodinane, and silica gel mediated oxidative ring-opening of aziridine to form alpha,beta-unsaturated ketone (allyl amine) and intramolecular Heck cyclization.

1,4-Conjugate addition of allyltrimethylsilane to α,β-unsaturated ketones

Abstract α,β-Unsaturated ketones smoothly undergo conjugate addition with allyltrimethylsilane in the presence of a catalytic amount of elemental iodine under very mild and convenient conditions to afford the corresponding Michael adducts in high yields with high selectivity.

Bi(OTf)3-catalyzed allylation of epoxides: a facile synthesis of homoallylic alcohols

Epoxides react smoothly with tetraallyltin in the presence of 2 mol% of Bi(OTf)3 under mild reaction conditions to afford the corresponding homoallylic alcohols in excellent yields with high regioselectivity while aryl aziridines produce exclusively allyl amines in good yields under similar conditions.

Unprecedented InCl3-catalyzed formation of cis-fused perhydrofuro[2,3-b]oxepines

Abstract 2-Methylindole and its N -substituted derivatives react smoothly with 2,3-dihydrofuran (DHF) in the presence of a catalytic amount of InCl 3 under mild conditions to afford the corresponding 2-methyl-3-perhydrofuro[2,3- b ]oxepin-4-yl-1 H -indole derivatives in fairly good yields with high diastereoselectivity, while 3,4-dihydro-2 H -pyran (DHP) affords exclusively 5,5-di(1 H -3-indolyl)-1-pentanol derivatives in high yields under similar reaction conditions.