Lagunamides are complex novel cyclic depsipeptides obtained from a marine cyanobacterium Lyngbya majuscula.  The lagunamides possess high antimalarial properties (IC50 0.19-0.91 mM) and significant cytotoxic properties against leukemia cell lines with (IC50 6.4-20.5 nM) respectively.  A highly convergent synthetic approach is utilized to solve the synthesis of these complex and interesting molecules. Asymmetric synthetic will be utilized in order to establish five of the 10 crucial stereo centers present in the molecular structure.  NMR spectroscopy, crystallography, optical rotations and LCMS will specifically be used to characterize all the intermediates needed for connecting these fragments to yield the lagunamides.  Stereoselective synthesis of several advanced intermediates crucial for the preparation of the lagunamides will be presented.  Specifically, one major fragment consisting of consecutive stereo centers has been prepared via a highly asymmetric route. The absolute stereochemistry (99% e.r.) of this intermediate obtained was confirmed using x-ray crystallography.

Synthesis of lagunamides: Antimalarial and cytotoxic natural products from the marine cyanobacterium lyngbya majuscula

243rd National Meeting (2012)

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