are ring-closing metathesis, Rubottom oxidation and Corey―Chaykovsky epoxidation. The subsequent transformations are carried out according to Barton's strategy to complete the total synthesis of (―)-ovalicin.
A newsynthesis of epoxyketone 22 is described that is a keyintermediate in Barton's synthesis of ovalicin (2), a powerful anti-angiogenetic inhibitor. The key process for the construction of 22 was ring-closing metathesis of olefins 11 and 12 obtained from 2,3:5,6-di-O-isopropylidene-α-d-mannofuranose (4) and regioselective desilylation of tri-TES ether 19. Furthermore, an alternative stereoselective
Total synthesis of (–)-ovalicin and analogues from<scp>L</scp>-quebrachitol
作者:Derek H. R. Barton、Sophie Bath、David C. Billington、Stephan D. Gero、Béatrice Quiclet-Sire、Mohammad Samadi
DOI:10.1039/p19950001551
日期:——
We describe here the first chiral totalsynthesis of (–)-ovalicin and the synthesis of several related analogues, from the naturally occurring cyclitol L-quebrachitol.
New spiroepoxide tetrahydrobenzo-triazoles and -imidazoles and their use as MetAP-II inhibitors
申请人:Deutsches Krebsforschungszentrum
公开号:EP2711367A1
公开(公告)日:2014-03-26
The present invention relates to new spiroepoxide tetrahydrobenzo-triazole and - imidazole compounds, a method for their production and their use as MetAP-II inhibitors, which are particularly useful as inhibitors of angiogenesis. The compounds are characterized by formula (I)
X=CorN
R1 = OC(O)R2 where R2 is alkyl, cycloalkyl, aryl, heteroaryl, or cinnamyl or
R1 = OC(O)NHR3 where R3 is alkyl, cycloalkyl, aryl, or heteroaryl
or
R1 = NHC(O)OR4 where R4 is alkyl
or
R1 = OH, NH2
R5 = alkyl, cycloalkyl, CH2R6 where R6 is aryl or heteroaryl