title: A diastereoselective oxa-Pictet-Spengler-based strategy for (+)-frenolicin B and epi-(+)-frenolicin B synthesis.
abstract: An efficient diastereoselective oxa-Pictet-Spengler reaction strategy was developed to construct benzoisochroman diastereomers. The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor analogs. The method is versatile and offers exquisite stereocontrol and, as such, offers a synthetic advance for the synthesis of pyranonaphthoquinone analogs.
authors.affiliation: Center for Pharmaceutical Research and Innovation, College of Pharmacy, University of Kentucky , 789 South Limestone Street, Lexington, Kentucky 40536, United States, and Division of Cardiovascular Medicine, Gill Heart Institute, and Markey Cancer Center, University of Kentucky , 741 South Limestone Street, Lexington, Kentucky 40536, United States.
authors.forename: Yinan
authors.initials: Y
authors.lastname: Zhang
authors.forename: Xiachang
authors.initials: X
authors.lastname: Wang
authors.forename: Manjula
authors.initials: M
authors.lastname: Sunkara
authors.forename: Qing
authors.initials: Q
authors.lastname: Ye
authors.forename: Larissa V
authors.initials: LV
authors.lastname: Ponomereva
authors.forename: Qing-Bai
authors.initials: QB
authors.lastname: She
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Morris
authors.forename: Jon S
authors.initials: JS
authors.lastname: Thorson
mesh_terms: D002839:Chromans / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D000095622:Benzoisochromanequinones
chemical_list: D002839:Chromans; D009285:Naphthoquinones; C018066:frenolicin B; D000095622:Benzoisochromanequinones