75207-13-5Relevant academic research and scientific papers
Convergent stereospecific total synthesis of monocillin I and radicicol: Some simplifications and improvements
Tichkowsky, Isabelle,Lett, Robert
, p. 3997 - 4001 (2007/10/03)
A much improved and reliable access to the macrolide 9, key-intermediate in our synthesis of monocillin I and radicicol is reported, via a modification of our first synthesis. The formation of the conjugated E,Z-dienone trans-epoxide is now achieved in a much higher yield, in a stereospecific reaction, by elimination of the methanesulfonate ester of the 6′-OH of the intermediate macrolide. It is also shown that the configuration of the 6′-OH has no significant incidence on all the steps leading to 9, and that consequently the two diastereoisomers 12, epimeric at 6′, can be used for the synthesis of radicicol.
Concise asymmetric syntheses of radicicol and monocillin I
Garbaccio,Stachel,Baeschlin,Danishefsky
, p. 10903 - 10908 (2007/10/03)
Radicicol (1) exhibits potent anticancer properties in vitro, which are likely to be mediated through its high affinity (20 nM) for the molecular chaperone Hsp90. Recently, we reported the results of a synthetic program targeting radicicol (1) and monocil
Convergent stereospecific total synthesis of Monocillin I and Monorden (or Radicicol)
Lampilas,Lett
, p. 777 - 780 (2007/10/02)
The first total syntheses of the antifungal resorcylic macrolides Monocillin I and Monorden (or Radicicol) have been achieved by a convergent stereospecific route. TBDMS phenol ethers were found to be suitable for all the scheme and were removed in the ul
