Syntheses of Ganoderma meroterpenoids (±)-spiroapplanatumine O and (±)-applanatumol B/W

Abstract

Total synthesis of (±)-applanatumol W, formal syntheses of (±)-spiroapplanatumine O and (±)-applanatumol B were accomplished using a common intermediate, methyl benzoyl cyclopentane carboxylate 9. This intermediate was synthesized through a one-pot reaction involving formation of Michael acceptor cyclopentenone through first Michael addition of malonate to acrolein, Aldol condensation and dehydration, followed by Michael addition of allylcuprate and subsequent demethoxycarboxylation.