A Model Study towards a Conceptually New Synthetic Entry into the Seco- and Heteroyohimbine Alkaloid Families

✍ Scribed by Thomas Vogelsang; Hans-Jürg Borschberg

• Book ID: 102256201
• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: German
• Weight: 219 KB
• Volume: 86
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200390303

✦ Synopsis

Abstract

A model study is presented that paves the way to a new and flexible synthetic approach towards the seco‐ and heteroyohimbine alkaloid class. The key step involves a highly diastereoselective Cope rearrangement of an (E,E)‐azacyclodeca‐3,7‐diene grafted onto a 3‐ethylindole moiety to furnish a trans‐3,4‐divinylpiperidine derivative in 83% yield.