A concise synthesis of (-)-centrolobine via a diastereoselective ring rearrangement metathesis-isomerisation sequence

Verena Böhrsch; Siegfried Blechert

doi:10.1039/b602056a

A concise synthesis of (-)-centrolobine via a diastereoselective ring rearrangement metathesis-isomerisation sequence

Chem Commun (Camb). 2006 May 14:(18):1968-70. doi: 10.1039/b602056a. Epub 2006 Mar 30.

Authors

Verena Böhrsch¹, Siegfried Blechert

Affiliation

¹ TU Berlin - Berlin University of Technology, Institute of Chemistry, Strasse des 17. Juni 115, Sekr. C3, 10623 Berlin, Germany.

PMID: 16767252
DOI: 10.1039/b602056a

Abstract

A total synthesis of (-)-centrolobine (1) based on a diastereoselective ring rearrangement metathesis-double bond isomerisation sequence and a one-pot cross metathesis-hydrogenation procedure is described.

Publication types

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

MeSH terms

Isomerism
Molecular Structure
Pyrans / chemical synthesis*
Pyrans / chemistry*

Substances

Pyrans
centrolobin