Work

Thermolysis of Isomigrastatin and Its Congeners via [3,3]-Sigmatropic Rearrangement: A New Route to the Synthesis of Migrastatin and Its Analogues

Year: 2006

Type: article

Abstract: Thermolysis of isomigrastatin (1) under neat heating conditions afforded migrastatin (1a). The reaction is proposed to proceed via a concerted [3,3]-sigmatropic rearrangement by which ring expansion is achieved regio- and enantiospecifically. The general applicability of this reaction was demonstrated with six additional isomigrastatin congeners (3-8), providing a new route to the synthesis of migrastatin analogues (3a-8a). [reaction: see text]

Source: Organic Letters

DOI: 10.1021/ol062470p

Authors: Jianhua Ju, Si-Kyu Lim, Hui Jiang, Jeong-Woo Seo, Yeng Her, Ben Shen

Institution: University of Wisconsin–Madison

Language: English

Topic: Chemical synthesis and pharmacological studies

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Cancer Institute, National Institute of Allergy and Infectious Diseases