Total synthesis of amaminol A: establishment of the absolute stereochemistry

Esa T T Kumpulainen; Ari M P Koskinen; Kari Rissanen

doi:10.1021/ol7022856

Total synthesis of amaminol A: establishment of the absolute stereochemistry

Org Lett. 2007 Nov 22;9(24):5043-5. doi: 10.1021/ol7022856. Epub 2007 Oct 23.

Authors

Esa T T Kumpulainen¹, Ari M P Koskinen, Kari Rissanen

Affiliation

¹ Laboratory of Organic Chemistry, Helsinki University of Technology, P.O. Box 6100, FI-02015 TKK, Espoo, Finland.

PMID: 17956115
DOI: 10.1021/ol7022856

Abstract

The first synthetic route to amaminol A with use of an organocatalytic intramolecular Diels-Alder reaction is reported. The absolute stereochemistry is proven with a crystallographic image of a cyclic carbamate of amaminol A.

MeSH terms

Amino Alcohols / chemical synthesis*
Amino Alcohols / chemistry
Bridged Bicyclo Compounds / chemical synthesis*
Bridged Bicyclo Compounds / chemistry
Carbamates / chemical synthesis*
Carbamates / chemistry
Crystallography, X-Ray
Models, Molecular
Molecular Structure
Stereoisomerism

Substances

Amino Alcohols
Bridged Bicyclo Compounds
Carbamates
amaminol A