Family-level stereoselective synthesis and biological evaluation of pyrrolomorpholine spiroketal natural product antioxidants† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc05505b Click here for additional data file.

نویسندگان

  • Alyssa L. Verano
  • Derek S. Tan
چکیده

The pyranose spiroketal natural products pollenopyrroside A and shensongine A (also known as xylapyrroside A, ent-capparisine B) have been synthesized by stereoselective spirocyclizations of a common C1-functionalized glycal precursor. In conjunction with our previously reported syntheses of the corresponding furanose isomers, this provides a versatile family-level synthesis of the pyrrolomorpholine spiroketal natural products and analogues. In rat mesangial cells, hyperglycemiainduced production of reactive oxygen species, which is implicated in diabetic nephropathy, was inhibited by pollenopyrroside A and shensongine A with mid-mM IC50 values, while unnatural C2-hydroxy analogues exhibited more potent, sub-mM activity.

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منابع مشابه

Family-level stereoselective synthesis and biological evaluation of pyrrolomorpholine spiroketal natural product antioxidants.

The pyranose spiroketal natural products pollenopyrroside A and shensongine A (also known as xylapyrroside A, ent-capparisine B) have been synthesized by stereoselective spirocyclizations of a common C1-functionalized glycal precursor. In conjunction with our previously reported syntheses of the corresponding furanose isomers, this provides a versatile family-level synthesis of the pyrrolomorph...

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First total synthesis of concavine† †Electronic supplementary information (ESI) available. CCDC 1523963. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc05627j Click here for additional data file. Click here for additional data file.

The synthesis of the unusual alkaloid concavine, isolated from Clitocybe concava (Basidiomycetae), has been accomplished. The synthetic route features regioand stereoselective manipulation of polycyclic imide intermediates via enolate substitution and Grignard addition, along with a key bridge-forming step involving a new method for sulfenylative radical cyclisation. The NMR data for synthetic ...

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A family of cis-macrocyclic diphosphines: modular, stereoselective synthesis and application in catalytic CO2/ethylene coupling† †Electronic supplementary information (ESI) available: Full experimental, crystallographic and spectroscopic data. CCDC 1477899–1477902. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc03614g Click here for additional data file. Click here for additional data file.

A family of cis-macrocyclic diphosphines: stereoselective synthesis and application in catalytic CO2/ethylene coupling Ioana Knopf,a Daniel Tofan,a Dirk Beetstra,b Abdulaziz Al-Nezari,b Khalid Al-Bahily,b and Christopher C. Cummins ∗,a a Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139-4307, USA b SABIC CRD, Fundamental Catalysis, Thuw...

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عنوان ژورنال:

دوره 8  شماره 

صفحات  -

تاریخ انتشار 2017