First synthesis of (±)-myristicyclin A

Shinichiro Kubo; Naoki Mori; Hidenori Watanabe; Hirosato Takikawa

doi:10.1080/09168451.2018.1495553

First synthesis of (±)-myristicyclin A

Biosci Biotechnol Biochem. 2018 Nov;82(11):1867-1870. doi: 10.1080/09168451.2018.1495553. Epub 2018 Jul 12.

Authors

Shinichiro Kubo¹, Naoki Mori¹, Hidenori Watanabe¹, Hirosato Takikawa¹

Affiliation

¹ a Department of Applied Biological Chemistry , Graduate School of Agricultural and Life Sciences, The University of Tokyo , Tokyo Japan.

PMID: 30001681
DOI: 10.1080/09168451.2018.1495553

Abstract

The first synthesis of myristicyclin A, which was isolated from the Papua New Guinean plant Horsfieldia spicata, is described. The synthesis features acid-mediated hydroarylation reaction to form a dihydrocoumarin moiety, construction of the 2,8-dioxabicyclo[3.3.1]nonane skeleton under acidic conditions, and regioselective Friedel-Crafts acylation at a later stage.

Keywords: Friedel-Crafts acylation; Synthesis; antimalarial; myristicyclin A.

MeSH terms

Acylation
Antimalarials / chemistry
Antimalarials / pharmacology
Antimalarials / therapeutic use
Carbon-13 Magnetic Resonance Spectroscopy
Catechin / chemical synthesis*
Catechin / chemistry
Catechin / therapeutic use
Inhibitory Concentration 50
Molecular Structure
Myristicaceae / chemistry*
Plasmodium falciparum / drug effects
Proton Magnetic Resonance Spectroscopy
Spectrometry, Mass, Electrospray Ionization

Substances

Antimalarials
myristicyclin A
Catechin