49749-51-1Relevant articles and documents
Construction of the cyclovibsanin core via a biogenetically modeled approach
Tilly, David P.,Williams, Craig M.,Bernhardt, Paul V.
, p. 5155 - 5157 (2005)
(Chemical Equation Presented) Construction of the 15-O-methylcyclovibsanin B core was achieved expediently in eight linear steps utilizing a biogenetically modeled approach.
Synthetic neovibsanes and their ability to induce neuronal differentiation in PC12 cells
Annette, P.-J. Chen,Müller, C. Catharina,Cooper, Helen M.,Williams, Craig M.
experimental part, p. 6842 - 6850 (2010/09/18)
A series of neovibsanin A and B derivatives and lower homologues were synthesized to study their neurotrophic ability with PC12 cells. 4,5-Bis-epi-neovibsanin A displayed prominent ability to induce neurite outgrowth compared to control cultures. Herein w
Towards the total synthesis of vibsanin E, 15-O-methylcyclovibsanin B, 3-hydroxyvibsanin E, furanovibsanin A, and 3-O-methylfuranovibsanin A
Schwartz, Brett D.,Tilly, David P.,Heim, Ralf,Wiedemann, Stefan,Williams, Craig M.,Bernhardt, Paul V.
, p. 3181 - 3192 (2007/10/03)
Studies detailing synthetic approaches to a variety of biosynthetically related vibsanin-type diterpenes (i.e. vibsanin E, 15-O-methylcyclovibsanin B, 3-hydroxy-vibsanin E, furanovibsanin A, and 3-O-methylfuranovibsanin A) are discussed. Biogenetically modelled approaches are coupled with an investigation of classical and modern six- to seven-membered ring-expansion protocols, which gain access to the central core of these natural products. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Expedient construction of the vibsanin E core without the use of protecting groups
Heim, Ralf,Wiedemann, Stefan,Williams, Craig M.,Bernhardt, Paul V.
, p. 1327 - 1329 (2007/10/03)
(Chemical Equation Presented) The tricyclic core of vibsanin E was constructed without the use of a protecting group in six steps. The El Gaied Baylis-Hillman variant was key to allowing the Bronsted acid induced tandem cyclization forming rings B and C i
Synthesis of carbocycles via intramolecular conjugate additions: Total syntheses of axane sesquiterpenoids
Guevel, Alyx-Caroline,Hart, David J.
, p. 473 - 479 (2007/10/02)
Syntheses of (±)-axamide-1 (2) and (±)-axisonitrile-1 (1) are described. The syntheses require 12 steps and 13 steps, respectively, from vinylogous ester 8 and feature the diastereoselective cyclization of unsaturated ester 7 to perhydroindan 5. Some interesting reactions of the organometallic derived from [(trimethylsilyl)methyl]magnesium chloride and cerium trichloride are also described.
