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Updated: Sep 17, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Total Synthesis of Daphenylline via Diels-Alder Cycloaddition and Rhodium-Catalyzed C-H Alkynylation
Wei Chen1, Aohang Liu1, Jinwei Huang1
1State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
None:
Daphenylline, a structurally intricate Daphniphyllum alkaloid, poses a formidable synthetic challenge due to its highly fused hexacyclic [6.6.5.7.6.5] framework and multiple stereocenters. Herein, we report an efficient total synthesis of daphenylline in 12 steps from known starting materials, featuring a key intramolecular Diels-Alder reaction, oxidative aromatization, Rh-catalyzed C-H alkynylation, and aldol condensation. Our approach leverages a carbonyl-directed C-H functionalization strategy to achieve regioselective alkynylation within a complex pentacyclic framework without the need for strongly coordinating directing groups.
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