title: Asymmetric Total Synthesis of Ieodomycin B.
abstract: Ieodomycin B, which shows in vitro antimicrobial activity, was isolated from a marineBacillusspecies. 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 ap-methoxybenzyl-protected aldehyde, as well as the generation of a lactone ring in a deprotection-lactonization one-pot reaction.
authors.affiliation: School of Pharmacy, Jiangxi Science and Technology Normal University, Fenglin Road 605, Nanchang 330013, China. linsj0317@163.com.
authors.forename: Shuangjie
authors.initials: S
authors.lastname: Lin
authors.affiliation: School of Pharmacy, Jiangxi Science and Technology Normal University, Fenglin Road 605, Nanchang 330013, China. 13979134167@163.com.
authors.forename: Jianting
authors.initials: J
authors.lastname: Zhang
authors.affiliation: School of Pharmacy, Jiangxi Science and Technology Normal University, Fenglin Road 605, Nanchang 330013, China. haozhangzhibin@163.com.
authors.forename: Zhibin
authors.initials: Z
authors.lastname: Zhang
authors.affiliation: School of Pharmacy, Jiangxi Science and Technology Normal University, Fenglin Road 605, Nanchang 330013, China. 18279111449@163.com.
authors.forename: Tianxiang
authors.initials: T
authors.lastname: Xu
authors.affiliation: School of Pharmacy, Jiangxi Science and Technology Normal University, Fenglin Road 605, Nanchang 330013, China. hsping02@gmail.com.
authors.forename: Shuangping
authors.initials: S
authors.lastname: Huang
authors.affiliation: School of Life Science, Jiangxi Science and Technology Normal University, Fenglin Road 605, Nanchang 330013, China. 13767101659@163.com.
authors.forename: Xiaoji
authors.initials: X
authors.lastname: Wang
mesh_terms: D000890:Anti-Infective Agents / Q000737:chemistry; D059001:Aquatic Organisms / Q000737:chemistry; D001407:Bacillus / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D011753:Pyrones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C584454:4-hydroxy-6-(3-methylhexa-3,5-dienyl)tetrahydropyran-2-one; D000890:Anti-Infective Agents; D007783:Lactones; D011753:Pyrones
keywords: antimicrobial; chelation-controlled Mukaiyama aldol reaction; ieodomycin B; total synthesis