Recent Syntheses and Strategies toward Polycyclic Gelsemium Alkaloids

Angew Chem Int Ed Engl. 2019 Jan 14;58(3):681-694. doi: 10.1002/anie.201807509. Epub 2018 Oct 31.

Abstract

This Minireview is focused on an in-depth discussion of comparative strategies to construct the gelsemine and gelsedine classes of the gelsemium alkaloids. This document highlights the diversity of strategies used to access specific motifs found within these targets: a) the fused "[3.2.1]bicycle" (in gelsemine) and "oxabicycle" (in gelsedine class); b) the "piroxindole" moiety with C7 quaternary center; c) the "N-heterocycles" and d) the "THP" moiety with C20 quaternary center (in gelsemine).

Keywords: alkaloids; natural products; synthesis design; terpenoids; total synthesis.

Publication types

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

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Bridged Bicyclo Compounds / chemical synthesis
  • Bridged Bicyclo Compounds / chemistry
  • Chemistry Techniques, Synthetic / methods*
  • Gelsemium / chemistry*
  • Oxindoles / chemical synthesis*
  • Oxindoles / chemistry
  • Polycyclic Compounds / chemical synthesis*
  • Polycyclic Compounds / chemistry

Substances

  • Alkaloids
  • Biological Products
  • Bridged Bicyclo Compounds
  • Oxindoles
  • Polycyclic Compounds
  • gelsedine
  • gelsemine