title: Total synthesis of diptoindonesin G and its analogues as selective modulators of estrogen receptors.
abstract: We have developed a versatile synthetic strategy for the synthesis of the natural product diptoindonesin G and its analogues as selective modulators of estrogen receptors. The strategy involves a regioselective dehydrative cyclization of arylacetals, a regioselective bromination of benzofurans, a sequential cross-coupling of bromo-benzofurans with aryl boronic acids, and a BBr3-mediated tandem cyclization and demethylation. Preliminary biological studies uncovered the critical and dispensable phenolic hydroxyl groups in the natural product and also revealed unexpected selectivity for isoforms of estrogen receptor.
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53705, USA and School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, 300072, P. R. China.
authors.forename: Ji-Tian
authors.initials: JT
authors.lastname: Liu
authors.affiliation: McArdle Laboratory for Cancer Research, Wisconsin Institute for Medical Research, University of Wisconsin-Madison, Madison, WI 53705, USA.
authors.forename: Truman J
authors.initials: TJ
authors.lastname: Do
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53705, USA and Department of Chemistry, University of Wisconsin-Madison, Madison, WI 53706, USA.
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Simmons
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53705, USA.
authors.forename: John C
authors.initials: JC
authors.lastname: Lynch
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53705, USA and Jiangsu Key Lab of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, PR China.
authors.forename: Wen
authors.initials: W
authors.lastname: Gu
authors.affiliation: Medicinal Chemistry Center, School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53706, USA. wtang@pharmacy.wisc.edu.
authors.forename: Zhi-Xiong
authors.initials: ZX
authors.lastname: Ma
authors.affiliation: McArdle Laboratory for Cancer Research, Wisconsin Institute for Medical Research, University of Wisconsin-Madison, Madison, WI 53705, USA.
authors.forename: Wei
authors.initials: W
authors.lastname: Xu
authors.affiliation: School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53705, USA and Department of Chemistry, University of Wisconsin-Madison, Madison, WI 53706, USA and Medicinal Chemistry Center, School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53706, USA. wtang@pharmacy.wisc.edu.
authors.forename: Weiping
authors.initials: W
authors.lastname: Tang
mesh_terms: D000080:Acetals / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D003500:Cyclization; D054879:Halogenation; D006801:Humans; D061986:MCF-7 Cells; D055550:Protein Stability / Q000187:drug effects; D011960:Receptors, Estrogen / Q000378:metabolism*; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D001572:Benzofurans; D001897:Boronic Acids; D011960:Receptors, Estrogen; C543798:diptoindonesin G