Total syntheses of the slime mold alkaloid arcyriacyanin A

✍ Scribed by Dr. Michael Brenner; Dr. Guido Mayer; Andreas Terpin; Prof. Dr. Wolfgang Steglich

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 543 KB
• Volume: 3
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.19970030112

✦ Synopsis

Abstract

Arcyriacyanin A (1) has been synthesized by three different routes. In the first synthesis the bisbromomagnesium salt of 2,4′‐biindole (5) was treated with dibromomaleimide (6) to yield arcyriacyanin A (1). The second approach used an intramolecular Heck reaction for the cyclization of a 4‐(triflyloxy)arcyriarubin 8 to N‐methylarcyriacyanin A (2). Thirdly, compound 2 was obtained by a domino Heck reaction between 3‐bromo‐4‐[1‐(tert‐butoxycarbonyl)indol‐3‐yl]‐1‐methylmaleimide (9) and 4‐bromoindole (10). The N‐methyl derivative 2 could be transformed into arcyriacyanin A (1) by standard methods.