Stereoselective Synthesis of Steroids and Related Compounds, V. Synthesis of (±)-Chokol A by a Tandem Michael-Addition/Dieckmann Cyclization

✍ Scribed by Groth, Ulrich ;Halfbrodt, Wolfgang ;Köhler, Thomas ;Kreye, Paul

• Book ID: 102901992
• Publisher: John Wiley and Sons
• Year: 1994
• Tongue: English
• Weight: 736 KB
• Volume: 1994
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199419940907

✦ Synopsis

Abstract

A total synthesis of (±)‐chokol A (rac‐12) was accomplished in five steps by starting from the α,β‐unsaturated ester (E)‐2 in an overall yield of 24%. The key step of this synthesis is the tandem conjugate addition/Dieckmann cyclization of the cuprate derived from vinyl bromide 9 with the α,β‐unsaturated ester (E)‐2.