First total synthesis of cassiarin A, a naturally occurring potent antiplasmodial alkaloid

Marcellino Rudyanto; Yuichiro Tomizawa; Hiroshi Morita; Toshio Honda

doi:10.1021/ol8004112

First total synthesis of cassiarin A, a naturally occurring potent antiplasmodial alkaloid

Org Lett. 2008 May 15;10(10):1921-2. doi: 10.1021/ol8004112. Epub 2008 Apr 16.

Authors

Marcellino Rudyanto¹, Yuichiro Tomizawa, Hiroshi Morita, Toshio Honda

Affiliation

¹ Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan.

PMID: 18412353
DOI: 10.1021/ol8004112

Abstract

The first total synthesis of cassiarin A, an antiplasmodial alkaloid isolated from Cassia siamea, was achieved via sequential alkynylation of arenes with Sonogashira coupling and 6- endo-dig-cyclization of phenolic oxygens to the resulting alkynes.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Antimalarials / chemical synthesis*
Antimalarials / chemistry
Cassia / chemistry
Heterocyclic Compounds, 3-Ring / chemical synthesis*
Heterocyclic Compounds, 3-Ring / chemistry
Molecular Structure

Substances

Alkaloids
Antimalarials
Heterocyclic Compounds, 3-Ring
cassiarin A