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Chem Sci. 2017 May 1;8(5):3687-3693. doi: 10.1039/c6sc05505b. Epub 2017 Mar 15.

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

Author information

1
Pharmacology Graduate Program , Weill Cornell Graduate School of Medical Sciences , Memorial Sloan Kettering Cancer Center , 1275 York Avenue, Box 422 , New York , NY 10065 , USA . Email: tand@mskcc.org.
2
Chemical Biology Program and Tri-Institutional Research Program , Memorial Sloan Kettering Cancer Center , 1275 York Avenue, Box 422 , New York , NY 10065 , USA.

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.

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