Concise Syntheses of Hyrtioreticulins C and D via a C-4 Pictet-Spengler Reaction: Revised Signs of Specific Rotations

J Nat Prod. 2017 Feb 24;80(2):241-245. doi: 10.1021/acs.jnatprod.7b00008. Epub 2017 Jan 30.

Abstract

The first syntheses of hyrtioreticulins C and D via a Pictet-Spengler reaction at the C-4 position of the indole rings are described. The synthesis proceeds in only two steps from commercially available starting materials. In this Communication, the structures of the natural products were confirmed. Furthermore, we revise the signs of the specific rotations of hyrtioreticulins C and D.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Cyclization
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry
  • Marine Biology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism

Substances

  • Biological Products
  • Indole Alkaloids
  • hyrtioreticulin C
  • hyrtioreticulin D