Journal
TETRAHEDRON
Volume 60, Issue 42, Pages 9405-9415Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2004.08.012
Keywords
total synthesis; natural product; bidensyneosides; glycosylation; protecting group effect
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Bidensyneosides are a group of five recently identified polyacetylenic glucosides from Bidens parviflora WILLD, a traditional Chinese medicinal plant that contains rich bioactive natural products. It was shown that bidensyneosides inhibited both histamine release and nitric oxide production. The synthesis of bidensyneoside A2 (2) and C (4) as well as 3-deoxybidensyneoside C (5) are described. These syntheses establish a synthetic entry to the bidensyneosides and confirm the stereochemistry at C3. Furthermore, a remarkable protecting Group effect on orthoester formation was observed during the glycosylation reaction. (C) 2004 Elsevier Ltd. All rights reserved.
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