Stereocontrolled semi-syntheses of deguelin and tephrosin
نویسندگان
چکیده
منابع مشابه
Stereocontrolled semi-syntheses of deguelin and tephrosin† †Electronic supplementary information (ESI) available: 1H and 13C NMR spectra. See DOI: 10.1039/c6ob02659a Click here for additional data file.
We describe stereocontrolled semi-syntheses of deguelin and tephrosin, anti-cancer rotenoids isolated from Tephrosia vogelii. Firstly, we present a new two-step transformation of rotenone into rot-2'-enonic acid via a zinc-mediated ring opening of rotenone hydrobromide. Secondly, following conversion of rot-2'-enonic acid into deguelin, a chromium-mediated hydroxylation provides tephrosin as a ...
متن کاملNovel stereocontrolled syntheses of tashiromine and epitashiromine
A novel stereocontrolled approach has been developed for the syntheses of tashiromine and epitashiromine alkaloids from cyclooctene β-amino acids. The synthetic concept is based on the azetidinone opening of a bicyclic β-lactam, followed by oxidative ring opening through ring C-C double bond and reductive ring-closure reactions of the cis- or trans-cyclooctene β-amino acids.
متن کاملStereocontrolled Synthesis of Polyfunctionalized cis-Decalins from 2-Methoxyphenols: Total Syntheses of (()-Eremopetasidione, (()-3â-Angeloyloxyfuranoeremophilane, and (()-3â-Methacryloyloxyfuranoeremophilane
A four-step stereocontrolled synthesis of polyfunctionalized cis-decalins is described, involving oxidation of 2-methoxyphenol, intermolecular Diels-Alder reaction, olefination, and Cope rearrangement. Application of this efficient strategy to the total syntheses of (()-eremopetasidione, (()-3â-angeloyloxyfuranoeremophilane, and (()-3â-methacryloyloxyfuranoeremophilane was accomplished from cre...
متن کاملStereocontrolled Syntheses of Piperidine Derivatives Using Diastereoselective Reactions of Chiral 1,3-Oxazolidines with Grignard Reagents: Asymmetric Syntheses of the Pinidine Enantiomers.
Pinidine is the main constituent of Pinus sabiniana and related plant species as determined, along with its chemical structure, by Tallent and co-workers over 40 years ag0.1 The complete stereochemistry of pinidine was unambiguously established by Hill to be la, usmg chemical and spectroscopic methods.2 Very recently, further work on the pinidine alkaloid contents of pine (Pinus) and spruce (Pi...
متن کاملStereocontrolled syntheses of all four stereoisomeric 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-hydroxynonenal.
[structure: see text]. trans-4-hydroxynonenal (4-HNE) is a unique product from the peroxidation of omega-6 polyunsaturated fatty acids. The major reaction of racemic 4-HNE with DNA is with deoxyguanosine to give four stereoisomeric exocyclic propano adducts. The stereospecific syntheses of these four adducts has been achieved at the nucleoside level. The synthetic approach is amenable to the sy...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Organic & Biomolecular Chemistry
سال: 2017
ISSN: 1477-0520,1477-0539
DOI: 10.1039/c6ob02659a