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Title: Synthesis of Nepetoidin B

Journal Article · · Synlett
 [1]; ORCiD logo [2];  [2];  [3];  [2]
  1. Univ. of Wisconsin, Madison, WI (United States); Department of Energy Great Lakes Bioenergy Research Center and Department of Biochemistry, the Wisconsin Energy Institute, University of Wisconsin
  2. Univ. of Wisconsin, Madison, WI (United States)
  3. USDA-ARS, Madison, WI (United States)
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Here the first synthesis of nepetoidin B in an overall yield of 17% was achieved in two steps through Baeyer–Villiger oxidation of commercially available 1,5-bis(3,4-dimethoxyphenyl)-1,4-pentadien-3-one with oxone to produce the tetramethylated nepetoidin B, followed by demethylation using boron tribromide.

Research Organization:
Great Lakes Bioenergy Research Center, Madison, WI (United States); Univ. of Wisconsin, Madison, WI (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
Grant/Contract Number:
FC02-07ER64494
OSTI ID:
1499008
Journal Information:
Synlett, Journal Name: Synlett Journal Issue: 09 Vol. 29; ISSN 0936-5214
Publisher:
ThiemeCopyright Statement
Country of Publication:
United States
Language:
English

References (16)

Chemical Constituents and Biological Activities of Nepeta Species journal October 2011
Pharmacological and chemical features ofNepetaL. genus: Its importance as a therapeutic agent journal October 2017
New phenolic compounds from Meehania urticifolia journal January 2011
Chemical composition of Ocimum sanctum by LC-ESI–MS/MS analysis and its protective effects against smoke induced lung and neuronal tissue damage in rats journal July 2017
Five new phenolic glycosides from Hedyotis scandens journal March 2013
Sebestenoids A–D, BACE1 inhibitors from Cordia sebestena journal December 2010
Neolignans as xanthine oxidase inhibitors from Hyptis rhomboides journal May 2014
Bioactive constituents from transformed root cultures of Nepeta teydea journal January 2017
The chemotaxonomic significance of two bioactive caffeic acid esters, nepetoidins A and B, in the Lamiaceae journal September 2003
Salvinorin A Analogs as Probes in Opioid Pharmacology journal May 2008
Neo-clerodane Diterpenes from the Hallucinogenic Sage Salvia divinorum journal November 2006
General Metal-Free Baeyer–Villiger-Type Synthesis of Vinyl Acetates journal May 2013
Two new labdane diterpenoids from the rhizomes ofIsodon yuennanensis journal November 2014
Two new potent inhibitors of xanthine oxidase from leaves of Perilla frutescens Britton var. acuta Kudo. journal January 1990
Natural Products from the Hallucinogenic Sage journal June 2010
A new flavonoid glycoside from Elsholtzia bodinieri text January 2016

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Baeyer–Villiger oxidation
demethylation
medicinal chemistry
natural products