A highly stereocontrolled total synthesis of (-)-neodysiherbaine A

Keisuke Takahashi; Takashi Matsumura; Graeme R M Corbin; Jun Ishihara; Susumi Hatakeyama

doi:10.1021/jo060410r

A highly stereocontrolled total synthesis of (-)-neodysiherbaine A

J Org Chem. 2006 May 26;71(11):4227-31. doi: 10.1021/jo060410r.

Authors

Keisuke Takahashi¹, Takashi Matsumura, Graeme R M Corbin, Jun Ishihara, Susumi Hatakeyama

Affiliation

¹ Graduate School of Biomedical Sciences, Nagasaki University, Nagasaki 852-8521, Japan.

PMID: 16709065
DOI: 10.1021/jo060410r

Abstract

Neodysiherbaine A, a neuroexitotoxin occurring in a Micronesian marine sponge Dysidea herbacea, was synthesized from tri-O-acetyl-D-glucal with excellent stereocontrol. The method established enables us to obtain gram quantities of neodysiherbaine A and its related compounds.

Publication types

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

MeSH terms

Alanine / analogs & derivatives*
Alanine / chemical synthesis
Animals
Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
Dysidea / chemistry
Molecular Structure

Substances

Bridged Bicyclo Compounds, Heterocyclic
neodysiherbaine A
Alanine