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

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Abstract

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, hyperglycemia-induced production of reactive oxygen species, which is implicated in diabetic nephropathy, was inhibited by pollenopyrroside A and shensongine A with mid-μM IC50 values, while unnatural C2-hydroxy analogues exhibited more potent, sub-μM activity.

Graphical abstract: Family-level stereoselective synthesis and biological evaluation of pyrrolomorpholine spiroketal natural product antioxidants

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Publication details

The article was received on 16 Dec 2016, accepted on 27 Feb 2017 and first published on 15 Mar 2017


Article type: Edge Article
DOI: 10.1039/C6SC05505B
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
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    Family-level stereoselective synthesis and biological evaluation of pyrrolomorpholine spiroketal natural product antioxidants

    A. L. Verano and D. S. Tan, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C6SC05505B

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