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Collective Total Synthesis of Four Ganoderma Meroterpenoids Based on an Intramolecular Aldol Strategy
Yasuhiro Meguro1, Mari Oyake1, Masaru Enomoto1
1Graduate School of Agricultural Science, Tohoku University, 468-1 Aramaki-Aza-Aoba, Aoba-ku, Sendai 980-0845, Japan.
Abstract:
The total synthesis of four Ganoderma meroterpenoids (lingzhiol, sinensilactam A, lingzhilactone B, and applanatumol I) has been accomplished from a known olefinic lactone in much shorter steps (4-8 steps) and markedly improved overall yields (15-27%) compared to previous syntheses. The key steps are highly regio- and diastereoselective intramolecular aldol reactions to prepare bicyclic lactone intermediates and a decarboxylative radical cyclization to install the unique tetracyclic ring system of lingzhiol.
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