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Regioselective Synthesis of Spiro-Ganoderma Meroterpenoid Motifs via Lewis Acid-Catalyzed Divergent Cycloadditions: [3 + 2] and Water Accelerated [5 + 2] Annulations.

For the first time, a water-driven Lewis acid-catalyzed [5 + 2] cyclization between allylsilanes and aurones was developed, affording spiro-Ganoderma-meroterpenoid (SGM) motifs with high yields and stereoselectivity. This method enables… Click to show full abstract

For the first time, a water-driven Lewis acid-catalyzed [5 + 2] cyclization between allylsilanes and aurones was developed, affording spiro-Ganoderma-meroterpenoid (SGM) motifs with high yields and stereoselectivity. This method enables efficient construction of spiro-tricyclic rings, introducing contiguous stereocenters without dry conditions or thermal/photoactivation. This approach revealed dual catalysts over the regio-control [3 + 2] spirocyclic ring creation by opposite functional group incorporation and halting at the interim stage, facilitating the synthesis of SGM scaffolds.

Keywords: spiro ganoderma; spiro; ganoderma meroterpenoid; water; lewis acid; acid catalyzed

Journal Title: Organic letters
Year Published: 2025

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