A highly efficient synthesis of the FGH ring of micrandilactone A. Application of thioureas as ligands in the Co-catalyzed Pauson-Khand reaction and Pd-catalyzed carbonylative annulation

Yefeng Tang; Yandong Zhang; Mingji Dai; Tuoping Luo; Lujiang Deng; Jiahua Chen; Zhen Yang

doi:10.1021/ol047394+

A highly efficient synthesis of the FGH ring of micrandilactone A. Application of thioureas as ligands in the Co-catalyzed Pauson-Khand reaction and Pd-catalyzed carbonylative annulation

Org Lett. 2005 Mar 3;7(5):885-8. doi: 10.1021/ol047394+.

Authors

Yefeng Tang¹, Yandong Zhang, Mingji Dai, Tuoping Luo, Lujiang Deng, Jiahua Chen, Zhen Yang

Affiliation

¹ Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Beijing 100871, China.

PMID: 15727466
DOI: 10.1021/ol047394+

Abstract

The functionalized FGH ring system of micrandilactone A was successfully constructed in high selectivity and good yields. The key reactions in our strategy are the Co-thiourea-catalyzed stereoselective, intramolecular Pauson-Khand reaction and Pd-thiourea-catalyzed stereoselective, intramolecular annulation. [structure: see text]

Publication types

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

MeSH terms

Catalysis
Cobalt / chemistry*
Crystallography, X-Ray
Lactones / chemical synthesis*
Lactones / chemistry*
Ligands
Molecular Conformation
Molecular Structure
Palladium / chemistry*
Plants, Medicinal / chemistry
Scutellaria / chemistry
Thiourea / analogs & derivatives*
Thiourea / chemistry*
Triterpenes / chemical synthesis*
Triterpenes / chemistry*

Substances

Lactones
Ligands
Triterpenes
micrandilactone A
Cobalt
Palladium
Thiourea