Isolation, Structure Elucidation, and Biomimetic Total Synthesis of Versicolamide B, and the Isolation of Antipodal (−)‐Stephacidin A and (+)‐Notoamide B from <i>Aspergillus versicolor</i> NRRL 35600

Abstract

Stereochemically unique: A new prenylated indole alkaloid, (+)-versicolamide B, has been isolated from cultures of Aspergillus versicolor NRRL 35600. The structure has been assigned by 2D NMR experiments, and confirmed by a biomimetic total synthesis. Versicolamide B is the first member of the paraherquamide/stephacidin family of alkaloids found to possess the anti relative stereochemistry at C19. ent-Stephacidin A and ent-notoamide B were also isolated for the first time. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z800106_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.