An expeditious Nazarov cyclization strategy toward the hydroazulene core of guanacastepene A

Pauline Chiu; Shuoliang Li

doi:10.1021/ol036433z

An expeditious Nazarov cyclization strategy toward the hydroazulene core of guanacastepene A

Org Lett. 2004 Feb 19;6(4):613-6. doi: 10.1021/ol036433z.

Authors

Pauline Chiu¹, Shuoliang Li

Affiliation

¹ Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. China. pchiu@hku.hk

PMID: 14961636
DOI: 10.1021/ol036433z

Abstract

The hydroazulene core of guanacastepene A has been synthesized in five steps from commercially available starting materials using a classical Nazarov cyclization to install the stereochemistry in the cyclopentanone diastereoselectively. In the presence or absence of Lewis bases, a hydroazulenone or a spirocyclic ketone generated via a novel Wagner-Meerwein rearrangement is obtained with excellent selectivity and yield.

Publication types

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

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Catalysis
Cyclization
Diterpenes / chemical synthesis*
Indicators and Reagents
Ketones / chemistry
Molecular Structure

Substances

Anti-Bacterial Agents
Diterpenes
Indicators and Reagents
Ketones
guanacastepene