Total synthesis of the proposed structure of cyclic hexadepsipeptide veraguamide A

Org Biomol Chem. 2012 Sep 21;10(35):7027-30. doi: 10.1039/c2ob26002f. Epub 2012 Aug 2.

Abstract

We have developed a practical method to assemble the proposed structure of natural product veraguamide A (1) by first preparing the three key fragments followed by optimization of the macrocyclization site. Although the synthetic product gave similar optical rotation to that reported for natural product, significant differences in the (1)H and (13)C NMR spectra were observed, especially the proton and carbon signals in the two N-MeVal moieties.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemical synthesis
  • Biological Products / chemistry*
  • Cyanobacteria / chemistry*
  • Depsipeptides / chemical synthesis
  • Depsipeptides / chemistry*
  • Magnetic Resonance Spectroscopy
  • Stereoisomerism

Substances

  • Biological Products
  • Depsipeptides
  • veraguamide A