939795-57-0Relevant academic research and scientific papers
Synthetic studies toward cytostatin, a natural product inhibitor of protein phosphatase 2A
Salit, Anne-Frédérique,Meyer, Christophe,Cossy, Janine,Delouvrié, Bénédicte,Hennequin, Laurent
, p. 6684 - 6697 (2008/12/20)
Synthetic approaches toward the natural product cytostatin, an inhibitor of protein phosphatase 2A possessing cytotoxic and antimetastatic activities, have been investigated. A formal synthesis of cytostatin has been achieved according to a strategy relyi
Total synthesis of discodermolide: Optimization of the effective synthetic route
De Lemos, Elsa,Poree, Francois-Hugues,Bourin, Arnaud,Barbion, Julien,Agouridas, Evangelos,Lannou, Marie-Isabelle,Commercon, Alain,Betzer, Jean-Francois,Pancrazi, Ange,Ardisson, Janick
experimental part, p. 11092 - 11112 (2009/11/30)
An efficient and modulable total synthesis of discodermolide (DDM), a unique marine anticancer polyketide is described including related alternative synthetic approaches. Particularly notable is the repeated application of a crotyltitanation reaction to yield homoallylic (Z)-O-ene-carbamate alcohols with excellent selectivity. Advantage was taken of this reaction not only for the stereocontrolled building of the syn-anti methyl-hydroxy- methyl triads of DDM, but also for the direct construction of the terminal (Z)diene. Of particular interest is also the installation of the C13=C14 (Z)-double bond through a highly selective dyotropic rearrangement. The preparation of the middle C8-C14 fragment in two sequential stages and its coupling to the C1-C7 moiety was a real challenge and required careful optimization. Several synthetic routes were explored to allow high and reliable yields. Due to the flexibility and robust character of this approach, it might enable a systematic structural variation of DDM and, therefore, the elaboration and exploration of novel discodermolide structural analogues.
