111222-90-3Relevant academic research and scientific papers
Synthesis of the Novel Anti-leukaemic Tetrahydrocyclopentabenzofuran, Rocaglamide and Related Synthetic Studies
Davey, Andrew E.,Schaeffer, Marcel J.,Taylor, Richard J. K.
, p. 2657 - 2666 (2007/10/02)
Two approaches to the rocaglamide tricyclic skeleton are described.The first, which employs an unusual dithianyl anion to carbonyl addition reaction, provides access to α-phenyl rocaglamide analogues.The second route involves an intramolecular keto aldehyde pinacolic coupling in the key step and can be used for the preparation of a whole range of rocaglamide analogues possessing both α- and β-phenyl substituents.A total synthesis of rocaglamide, in racemic form, is described using this second approach.The synthetic route commences with phloroglucinol, an inexpensive and readily-available starting material, and takes only 8/9 steps giving an overall yield > 6percent.The synthesis of 1-epi-rocaglamide 29b is also described.
A Novel 1,3-Dithiane-based Cyclopenta-annellation Procedure: Synthesis of the Rocaglamide Skeleton
Davey, Andrew E.,Taylor, Richard J. K.
, p. 25 - 27 (2007/10/02)
A novel three carbon cyclopentanone annellation procedure, based on direct 1,3-dithiane lithiation followed by intramolecular carbonyl addition, has been employed in a synthetic approach to the anti-cancer compound, rocaglamide.
