Abstract
Ieodomycin B, which shows in vitro antimicrobial activity, was isolated from a marine Bacillus species. A novel asymmetric total synthetic approach to ieodomycin B using commercially available geraniol was achieved. The approach involves the generation of 1,3-trans-dihydroxyl at C-3 and C-5 positions via a Crimmins-modified Evans aldol reaction and a chelation-controlled Mukaiyama aldol reaction of a p-methoxybenzyl-protected aldehyde, as well as the generation of a lactone ring in a deprotection–lactonization one-pot reaction.
Highlights
Natural products are an important resource for drug discovery
1.1.Reported total ofieodomycin ieodomycin and on obtaining the natural product at a higher optical purity, we focused on the total synthesis of
Mukaiyama reaction in the synthesis of ieodomycin we performed our analysis based aldol on this strategy, as total depicted in Scheme
Summary
Natural products are an important resource for drug discovery. Isolation, identification, and syntheses of these products or their derivatives, as well as their subsequent biological studies are of interest. Goswami and coworkers achieved pentyne‐1‐ol [8] This route involves a Crimmins‐modified Evans aldol reaction and a nucleophilic ends in a 1,3‐reduction, affording the desired chiral centers. Evans addition of thestarting potassium salt monomethyl forming δ‐hydroxyl β‐keto ester It ieodomycin B in nine linear steps starting from the same alcohol. In their route, they used the aldol reaction twice to construct the two chiral hydroxyls [9]. Crimmins‐modified Evans aldol reaction twice to construct the two chiral hydroxyls [9].4+Recently, total synthesis of ieodomycin involving seven steps this approach, used. In on continuation of natural our studies on developing a newpurity, approach towardon thethe synthesis of lactones and obtaining the product at a higher optical we focused total synthesis of effective protocol to its total synthesis is important. It is well‐known that chelation‐controlled andieodomycin on obtaining the natural a higher purity, we focused the total synthesis
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