Issue 8, 2014

Highly efficient and stereocontrolled oxidative coupling of tetrahydropyrroloindoles: synthesis of chimonanthines, (+)-WIN 64821 and (+)-WIN 64745

Abstract

The highly efficient and stereocontrolled dimerization of 1,2,3,8-tetrahydropyrrolo[2,3-b]indoles was successfully developed with I2 as the oxidant, which allowed the rapid synthesis of meso- and rac-chimonanthines, (+)-WIN 64821 and (+)-WIN 64745 in the highest overall yields to date via the oxidation–oxidation–reduction sequence.

Graphical abstract: Highly efficient and stereocontrolled oxidative coupling of tetrahydropyrroloindoles: synthesis of chimonanthines, (+)-WIN 64821 and (+)-WIN 64745

Supplementary files

Article information

Article type
Research Article
Submitted
07 jun 2014
Accepted
23 jul 2014
First published
25 jul 2014

Org. Chem. Front., 2014,1, 956-960

Author version available

Highly efficient and stereocontrolled oxidative coupling of tetrahydropyrroloindoles: synthesis of chimonanthines, (+)-WIN 64821 and (+)-WIN 64745

D. Sun, C. Xing, X. Wang, Z. Su and C. Li, Org. Chem. Front., 2014, 1, 956 DOI: 10.1039/C4QO00165F

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