Scripps VIVO scripps research logo

  • Index
  • Log in
  • Home
  • People
  • Organizations
  • Research
  • Events
Search form

Total synthesis, revised structure, and biological evaluation of biyouyanagin A and analogues thereof

Academic Article
uri icon
  • Overview
  • Identity
  • Additional Document Info
  • View All
scroll to property group menus

Overview

related to degree

  • Sarlah, David, Ph.D. in Chemistry, Scripps Research 2006 - 2011

authors

  • Nicolaou, K.C.
  • Wu, T. R.
  • Sarlah, David
  • Shaw, D. M.
  • Rowcliffe, E.
  • Burton, Dennis

publication date

  • August 2008

journal

  • Journal of the American Chemical Society  Journal

abstract

  • Isolated from Hypericum species H. chinese L. var. salicifolium, biyouyanagin A was assigned structure 1a or 1b on the basis of NMR spectroscopic analysis. This novel natural product exhibited significant anti-HIV properties and inhibition of lipopolysaccharide-induced cytokine production. Described herein are the total syntheses of biyouyanagin A and several analogues (3-11), structural revision of biyouyanagin A to 2b, and the biological properties of all synthesized compounds. The total synthesis proceeded through cascade sequences that efficiently produced enantiomerically pure key building blocks 15b (ent-zingiberene) and 18 (hyperolactone C) and featured a novel [2 + 2] photoinduced cycloaddition reaction which occurred with complete regio- and stereoselectivity. Biological investigations with the synthesized biyouyangagins A (2-11) and hyperolactones C (12-16) revealed that the activity of biyouyanagin A most likely resides in its hyperolactone C structural domain.

subject areas

  • Anti-HIV Agents
  • Cell Line
  • Cell Proliferation
  • Crystallography, X-Ray
  • Cytokines
  • Drug Evaluation, Preclinical
  • Furans
  • HIV
  • Humans
  • Hypericum
  • Inhibitory Concentration 50
  • Lipopolysaccharides
  • Lymphocytes
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Conformation
  • Sensitivity and Specificity
  • Sesquiterpenes
  • Spiro Compounds
  • Stereoisomerism
scroll to property group menus

Identity

PubMed Central ID

  • PMC2614900

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja802805c

PubMed ID

  • 18646750
scroll to property group menus

Additional Document Info

start page

  • 11114

end page

  • 11121

volume

  • 130

issue

  • 33

©2021 The Scripps Research Institute | Terms of Use | Powered by VIVO

  • About
  • Contact Us
  • Support