950765-12-5Relevant academic research and scientific papers
Total synthesis and biological evaluation of amphidinolide v and analogues
Fuerstner, Alois,Fluegge, Susanne,Larionov, Oleg,Takahashi, Yohei,Kubota, Takaaki,Kobayashi, Junichi
experimental part, p. 4011 - 4029 (2009/12/24)
A sequence of ring-closing alkyne metathesis followed by an inter-molecular enyne metathesis of the resulting cyeloalkyne with ethene was used to forge the macrocyclic skeleton and to set the vicinal exo-methylene branches characteristic for the cytotox-ic marine natural product amphidino-lide V (1). Comparison of the synthetic material with an authentic sample of this extremely scarce metabolite isolated from a dinoflagellate of the Amphi- dinium sp. eliminated any doubts about its structure and allowed the absolute configuration of amphidinolide V to be determined as 8R,9S,10S,13R. Moreover, the flexibility inherent to the underlying synthesis blueprint also opened access to a comprehensive set of diastereomers of 1 as well as to synthetic analogues differing from the natural lead in the lipophilic chains appended to the macrocyclic core. This set of designed analogues gave first insights into structure-activity relationships, which revealed that the stereo-structure of the macrolactone is a highly critical parameter, whereas the examined alterations of the side chain did not diminish the cytotoxicity of the compounds to any notable extent.
What is amphidinolide V? Report on a likely conquest
Fuerstner, Alois,Larionov, Oleg,Fluegge, Susanne
, p. 5545 - 5548 (2008/09/17)
(Chemical Equation Presented) The awesome power of metathesis is reflected in the synthesis of the proposed structure of the cytotoxic natural product amphidinolide V, as well as of all other stereomers containing a trans-epoxide unit. It can be concluded
