An efficient method for construction of the angularly fused 6,3,5-tricyclic skeleton of mycorrhizin A and its analogues

Binxun Yu; Tuo Jiang; Weiguo Quan; Junpeng Li; Xinfu Pan; Xuegong She

doi:10.1021/ol8026895

An efficient method for construction of the angularly fused 6,3,5-tricyclic skeleton of mycorrhizin A and its analogues

Org Lett. 2009 Feb 5;11(3):629-32. doi: 10.1021/ol8026895.

Authors

Binxun Yu¹, Tuo Jiang, Weiguo Quan, Junpeng Li, Xinfu Pan, Xuegong She

Affiliation

¹ Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, PR China.

PMID: 19175348
DOI: 10.1021/ol8026895

Abstract

The angularly fused 6,3,5-tricyclic system is readily generated via a cascade cyclization under acid promotion. The reaction proceeds at room temperature with high stereochemical fidelity from the electrophilic center of the epoxide to the cyclopropane product. This methodology provides a potentially useful approach for the synthesis of mycorrhizin A and its analogues.

Publication types

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

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry
Biological Products / chemical synthesis*
Biological Products / chemistry
Combinatorial Chemistry Techniques
Coumarins / chemical synthesis*
Coumarins / chemistry
Cyclization
Molecular Structure

Substances

Anti-Bacterial Agents
Biological Products
Coumarins
mycorrhizin A