Title
Total Synthesis and Biological Evaluation of Heliolactone
Author
Masahiko Yoshimura, Raymonde Fonné‐Pfister, Claudio Screpanti, Katrin Hermann, Stefano Rendine, Michael Dieckmann, Pierre Quinodoz, Alain De Mesmaeker
Year
2019
Journal
Helvetica Chimica Acta
Abstract
Strigolactones are phytohormones, which affect diverse aspects of plant growth and development with potential application in modern agriculture. Recently, heliolactone has been isolated as a non‐canonical type of strigolactone from the root exudates of sunflower, and it could be involved in signaling in the rhizosphere as well as in planta. However, its biological activity is yet to be evaluated, due to its relative chemical instability and its low natural abundance. Herein, we describe the gram‐scale synthesis of heliolactone and its derivatives by using Stille cross‐coupling as the key bond‐forming reaction, and we disclose some of their biological activities (soil stability, binding ability to strigolactone receptor, corn germination, sunflower germination, Orobanche cumana germination and leaf senescence) in comparison with other canonical and non‐canonical strigolactones.
Instrument
J-1500
Keywords
Circular dichroism, Absolute configuration, Stereochemistry, Organic chemistry, Agriculture and environmental