Direct imine acylation: synthesis of the proposed structures of 'upenamide

William P Unsworth; Katherine A Gallagher; Mickaël Jean; Jan Peter Schmidt; Louis J Diorazio; Richard J K Taylor

doi:10.1021/ol3030764

Direct imine acylation: synthesis of the proposed structures of 'upenamide

Org Lett. 2013 Jan 18;15(2):262-5. doi: 10.1021/ol3030764. Epub 2012 Dec 24.

Authors

William P Unsworth¹, Katherine A Gallagher, Mickaël Jean, Jan Peter Schmidt, Louis J Diorazio, Richard J K Taylor

Affiliation

¹ Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.

PMID: 23265326
DOI: 10.1021/ol3030764

Abstract

The synthesis of the two proposed structures of macrocyclic marine natural product 'upenamide is reported. The key step utilizes direct imine acylation (DIA) with a protected β-hydroxy acid to construct the key tricyclic ABC ring system. The macrocyclization was completed in the final step using a Stille cross-coupling reaction.

Publication types

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

MeSH terms

Acylation
Animals
Biological Products / chemical synthesis*
Biological Products / chemistry
Imines / chemistry*
Indonesia
Marine Biology
Molecular Structure
Porifera / chemistry
Quinolizines / chemical synthesis*
Quinolizines / chemistry
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry
Stereoisomerism

Substances

Biological Products
Imines
Quinolizines
Spiro Compounds
upenamide