Synthetic approaches to pseudopterosin

Gill, Simon David (1991) Synthetic approaches to pseudopterosin. University of Southampton, Doctoral Thesis.

Abstract

Two synthetic approaches to the marine diterpenoid monosaccharides called the pseudopterosins are described. The first approach achieved control of two of the chiral centres of the pseudopterosins by performing an intramolecular hydroboration/carbonylation reaction on (S)-limonene.

The second approach achieved control of all of the chiral centres by using an intramolecular directed hydroboration reaction. The aromatic ring was formed using an aromatic annulation reaction developed by R. K. Dieter. The functionality on the aromatic ring was adjusted using a novel reductive cleavage reaction. Closure of the third ring was achieved using a Houben-Hoesch reaction, forming an advanced intermediate which has already been transformed into pseudopterosins A and E by E. J. Corey. The methods of preparing the different isomers of the aglycone fragment of all of the pseudopterosins are also presented.

The scope of the aromatic annulation reaction and the cleavage reactions is discussed, along with a novel method of preparing either enantiomer of isopulegol and neoisopulegol from citronellol.

A review of the discovery, biological properties and previous syntheses of the pseudopterosins is also presented.

This record has no associated files available for download.

Contributors

Download statistics