Muricatacin, a Gateway Molecule to Higher Acetogenin Synthesis

Chem Asian J. 2020 Nov 16;15(22):3660-3681. doi: 10.1002/asia.202000955. Epub 2020 Oct 9.

Abstract

In this review, we have abstracted the various syntheses of acetogenins where the start point has been muricatacin. The latter can best be synthesized in either enantiomer form by the Sharpless method in three steps and can be admired as a gateway molecule for a quick assembly of many higher acetogenins. Muricatacin with orthogonally differentiated hydroxy groups and the available lactone carbonyl for chain elongation/modification can enable the concise synthesis of higher acetogenins. Many closely related synthetic intermediates possible from muricatacin are also abstracted here. The review should give impetus for future synthetic endeavours where the start point could be muricatacin and at least to the new molecules that are yet to be synthesized.

Keywords: Acetogenins; Anticancer activity; Muricatacin; Natural Products; Tetrahydrofurans; Total synthesis.

Publication types

  • Review

MeSH terms

  • Acetogenins / chemical synthesis*
  • Acetogenins / chemistry
  • Furans / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Acetogenins
  • Furans
  • muricatacin