title: First total synthesis of antihypertensive natural products S-(+)-XJP and R-(-)-XJP.
abstract: The first asymmetric total synthesis of antihypertensive natural products S-(+)-XJP and R-(-)-XJP has been achieved in 8 steps starting from commercially available 6-bromo-2-hydroxy-3-methoxybenzaldehyde. Key steps included intramolecular Heck reaction and oxidative ozonolysis reaction with the retention of stereochemistry. A latent functionality strategy was implemented to circumvent the racemization in this endeavor. The protocol described here provided a fast and easily accessible synthetic method to obtain optically pure isochroman-4-one derivatives. Furthermore, the in vivo antihypertensive effects of (±)-XJP, S-(+)-XJP and R-(-)-XJP were investigated on spontaneously hypertensive rats. The obtained results could provide valuable information to identify a promising lead for further chemical modification research.
authors.affiliation: State Key Laboratory of Natural Medicines, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, PR China. jinyixu@china.com cpu-jill@163.com.
authors.forename: Chaolei
authors.initials: C
authors.lastname: Wang
authors.forename: Guoxiang
authors.initials: G
authors.lastname: Wei
authors.forename: Xue
authors.initials: X
authors.lastname: Yang
authors.forename: Hequan
authors.initials: H
authors.lastname: Yao
authors.forename: Jieyun
authors.initials: J
authors.lastname: Jiang
authors.forename: Jie
authors.initials: J
authors.lastname: Liu
authors.forename: Mingqin
authors.initials: M
authors.lastname: Shen
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Wu
authors.forename: Jinyi
authors.initials: J
authors.lastname: Xu
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C000591230:7,8-dihydroxy-3-methylisochroman-4-one; D001578:Benzopyrans; D001688:Biological Products