62497-62-5Relevant academic research and scientific papers
Total synthesis of PDE-I and -II by copper-mediated double aryl amination This paper is dedicated to Professor Teruaki Mukaiyama in celebration of the 40th anniversary of the Mukaiyama aldol reaction
Okano, Kentaro,Mitsuhashi, Nakako,Tokuyama, Hidetoshi
, p. 10946 - 10954 (2014/01/06)
A concise total synthesis of PDE-I and -II featuring copper-mediated double aryl amination with the combination of CuI, CsOAc, and Cs2CO 3 is described. The highly substituted pyrroloindole skeleton was constructed by a one-pot five-step sequence including double aryl amination, β-elimination, deprotection of a Cbz group, and unexpected formation of an indole via removal of an Ns group followed by rearomatization. The undesired elimination of the protecting group (Ns group) was hampered by using the Boc group as a protecting group in the second-generation synthesis, which excluded the reduction of the indole required in the first-generation synthesis.
Vinyl Azides in Heterocyclic Synthesis. Part 8. Synthesis of the Naturally Occuring Phosphodiesterase Inhibitors PDE-I and PDE-II
Bolton, Richard E.,Moody, Christopher, J.,Rees, Charles W.,Tojo, Gabriel
, p. 931 - 936 (2007/10/02)
The synthesis of the naturally occuring pyrroloindole phosphodiesterase inhibitors PDE-I (1) and PDE-II (2) from isovanillin is described.The route involves the construction of both pyrrole rings by vinylnitrene cyclisations, the key cyclisation substrates being the azidoacrylates (5) and (11), prepared from the aldehydes (4) and (10) respectively.The tricyclic intermediate (12) is converted into both PDE-I and PDE-II by selective reduction, followed by carbamoylation or acetylation respectively, and deprotection.
Studies on the Synthesis of the Antitumor Agent CC-1065. Synthesis of PDE I and PDE II, Inhibitors of Cyclic Adenosine-3',5'-monophosphate Phosphodiesterase Using the 3,3'-Bipyrrole Strategy
Carter, Paul,Fitzjohn, Steven,Halazy, Serge,Magnus, Philip
, p. 2711 - 2717 (2007/10/02)
In the model series tert-butyl 2,4-pentadienoate was treated with TosCHMeNC/NaH to give the pyrrole 18, which was converted into the 3,3'-bipyrrole 20.Treatment of the pyrrole 20 with oxalyl chloride gave the o-quinone 21, which was reduced and concomitan
Synthesis of the Phosphodiesterase Inhibitors PDE-I and PDE-II
Bolton, Richard E.,Moody, Christopher J.,Rees, Charles W.,Tojo, Gabriel
, p. 1775 - 1776 (2007/10/02)
The pyrroloindole phosphodiesterase inhibitors PDE-I (1) and PDE-II (2) have been synthesised from isovanilin by a route which involves construction of both pyrrole rings by thermolysis of azidoacrylates readily derived from benzaldehydes.
