Synthesis of integerrimide A by an on-resin tandem Fmoc-deprotection-macrocyclisation approach

Org Biomol Chem. 2013 Nov 28;11(44):7760-7. doi: 10.1039/c3ob41447g. Epub 2013 Oct 11.

Abstract

A solid-phase total synthesis of integerrimide A (1) is reported. This work employs a safety-catch linker which enables head-to-tail cyclisation of the required linear peptide 6 as a method of cleaving the peptide from the solid support, and highlights a new tandem approach to direct macrocyclisation. It provides access to useful quantities of 1 in 16 steps and 19% overall yield, based on the manufacturer's stated resin substitution from commercially available materials, and also verifies the absolute stereochemistry of the natural product.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization*
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry
  • Solid-Phase Synthesis Techniques

Substances

  • Peptides, Cyclic
  • integerrimide A