title: The first asymmetric synthesis of marliolide from readily accessible carbohydrate as chiral template.
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.
authors.affiliation: College of Pharmacy and Integrated Research Institute for Drug Development, Dongguk University-Seoul, Goyang, 410-820, Republic of Korea.
authors.forename: Karabasappa
authors.initials: K
authors.lastname: Mailar
authors.affiliation: College of Pharmacy and Integrated Research Institute for Drug Development, Dongguk University-Seoul, Goyang, 410-820, Republic of Korea. Electronic address: mp89@dongguk.edu.
authors.forename: Won Jun
authors.initials: WJ
authors.lastname: Choi
mesh_terms: D015107:4-Butyrolactone / Q000138:chemical synthesis / Q000737:chemistry; D000478:Alkylation; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D015107:4-Butyrolactone
keywords: Asymmetric synthesis; Lactone enolate alkylation; Marliolide; γ-butyrolactone