2. Academic Validation
  3. synthesis and biological evaluation of fully functionalized seco-pancratistatin analogues

synthesis and biological evaluation of fully functionalized seco-pancratistatin analogues

  • J Nat Prod. 2008 Mar;71(3):357-63. doi: 10.1021/np0705460.
James McNulty 1,  Jerald J Nair,  Carly Griffin,  Siyaram Pandey
Affiliations

Affiliation

  • 1 Department of Chemistry, McMaster University, Hamilton, Ontario, Canada. [email protected]
PMID: 18225861 DOI: 10.1021/np0705460
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.

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