Abstract

(-)-Chamaecydin and (-)-isochamaecydin, two uncommon C30 terpenoids comprising abietane-type diterpenes and thujane-type monoterpenes, were achieved from β-pinene with (-)-sabinene in 18 and 20 steps, respectively. Key steps include a Claisen-Ireland rearrangement to establish the all-carbon quaternary center, a Rh catalyzed C-H bond insertion reaction to install a spiro-five-membered ring and a Lewis acid promoted cyclization of polyenes to construct the two six-membered rings.

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