Toward a structure-activity relationship for apoptolidin: selective functionalization of the hydroxyl group array

Org Lett. 2003 Feb 20;5(4):487-90. doi: 10.1021/ol027366w.

Abstract

[reaction: see text] To investigate the structural basis for the exceptional selectivity and activity of apoptolidin (1), a strategy has been devised that allows for selective functionalization of seven of its eight hydroxyl groups based on progressive silyl protection, derivatization, and deprotection. The syntheses of these derivatives and their ability to inhibit F(0)F(1)-ATPase are reported.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology*
  • Humans
  • Hydroxylation
  • Inhibitory Concentration 50
  • Macrolides*
  • Mitochondrial Proteins
  • Proton-Translocating ATPases / antagonists & inhibitors
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Macrolides
  • Mitochondrial Proteins
  • Proton-Translocating ATPases
  • apoptolidin