Related Experiment Video
Updated: Mar 18, 2026

Rapid One-step Enzymatic Synthesis and All-aqueous Purification of Trehalose Analogues
Published on: February 17, 2017
The first asymmetric synthesis of marliolide from readily accessible carbohydrate as chiral template
Karabasappa Mailar1, Won Jun Choi1
1College of Pharmacy and Integrated Research Institute for Drug Development, Dongguk University-Seoul, Goyang, 410-820, Republic of Korea.
Abstract:
A simple and efficient strategy for the first asymmetric total synthesis of marliolide was accomplished by using stereoselective alkylation of the dianion of the β-hydroxy lactone enolate with myristyl aldehyde as a key step. The key intermediate, β-hydroxyl γ-methyl butyrolactone was prepared by transformation of L-lyxonolactone starting from D-ribose, a naturally abundant chiral carbohydrate.
Related Concept Videos
Biosynthesis of Polysaccharides
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Biosynthesis of Lipids
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Preparation of Alcohols via Substitution Reactions
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...

