Document Report Card

ID: ALA1144786

Journal: J Nat Prod

Title: synthesis and biological evaluation of fully functionalized seco-pancratistatin analogues.

Authors: McNulty J, Nair JJ, Griffin C, Pandey S.

Abstract: The total synthesis of fully functionalized polyhydroxyamide B,C- seco-analogues of the anticancer compound pancratistatin (PST) ( 1) is reported. Key steps include an Evans' MgCl 2-promoted anti-aldol reaction between a functionalized l-threose derivative and ( R)-(+)-oxazolidinone to stereoselectively form the C-1/C-10b bond and a regiospecific radical-mediated oxidative fragmentation of a 1,3-benzylidene. The B,C- seco compounds 25 and 26 exhibited low activity (ED 50 > 30 microg/mL) for inducing apoptosis in human cancer cells.

CiteXplore: 18225861

DOI: 10.1021/np0705460