Synthesis of Amaryllidaceae Constituents and Unnatural Derivatives

Angew Chem Int Ed Engl. 2016 May 4;55(19):5642-91. doi: 10.1002/anie.201508227. Epub 2016 Mar 11.

Abstract

This update covers the syntheses of Amaryllidaceae alkaloids since the publication of the last major review in 2008. A short summary of past syntheses and their step count is provided for the major constituents; pancratistatin, 7-deoxypancratistatin, narciclasine, lycoricidine, lycorine, and for other natural constituents, as well as for unnatural derivatives. Discussion of biological activities is provided for unnatural derivatives. Future prospects and further developments in this area are covered at the end of the review. The literature is covered to the end of August 2015.

Keywords: Amaryllidaceae alkaloids; anticancer drugs; biological activity; structure-activity relationship; 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
  • Amaryllidaceae / chemistry*
  • Amaryllidaceae / metabolism
  • Amaryllidaceae Alkaloids / chemical synthesis
  • Amaryllidaceae Alkaloids / chemistry
  • Antineoplastic Agents, Phytogenic / chemical synthesis
  • Antineoplastic Agents, Phytogenic / chemistry
  • Isoquinolines / chemical synthesis
  • Isoquinolines / chemistry
  • Phenanthridines / chemical synthesis
  • Phenanthridines / chemistry
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Alkaloids
  • Amaryllidaceae Alkaloids
  • Antineoplastic Agents, Phytogenic
  • Isoquinolines
  • Phenanthridines
  • lycoricidine
  • narciclasine
  • pancratistatin
  • lycorine