Total synthesis of the reported structure of 13a-hydroxytylophorine

Sci Rep. 2017 Dec 5;7(1):16916. doi: 10.1038/s41598-017-17015-8.

Abstract

The first total synthesis of the reported structure of 13a-hydroxytylophorine was accomplished. The key step was an unprecedented NaBH4-promoted one-pot reductive cyclization cascade that efficiently yielded a hydroxyl azonane intermediate. The indolizidine framework was obtained by means of oxidation and a subsequent unexpected protecting-group migration. This total synthesis revealed that the reported structure of the naturally isolated compound is incorrect.

Publication types

  • Research Support, Non-U.S. Gov't