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Gibberellin A18甲酯的简短全合成 Concise Synthesis of (−)-GA18 Methyl Ester
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Gibberelins play a critical role for plants and mankind being vital factors for plant growth and agriculture. They are the reason why we avoided a global hunger wave in the 20th century, and their analogs could open new mechanisms of action against cancer! This makes synthetic access and further biochemical and pharmacological studies even more important. In this video, we will introduce a paper about concise synthesis of (−)-GA18 methyl ester. This paper was recently published on JACS by Mingji Dai and co-workers. The key features includes an intramolecular ene reaction to form the C ring, an oxidative cleavage followed by aldol condensation to realize a ring contraction and form the challenging trans-hydrindane (AB ring), and a photochemical [2+2] cycloaddition accompanied by a subsequent SmI2-mediated skeletal rearrangement to construct the methylenebicyclo[3.2.1]octanol moiety (CD ring).
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