Synthetic studies toward the kempane diterpenes. Diels–Alder additions to bicyclic dienes

C Liu, G Bao, DJ Burnell

Index: Liu, Chunjian; Bao, Guanglin; Burnell, D. Jean Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 20 p. 2644 - 2656

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Abstract

Diels–Alder additions of 2, 6-dimethyl-p-benzoquinone to the bicyclic dienes 24, 30 and 32 took place with very high regio-, stereo-and facial selectivity. Reduction and then alkylation of a tetracyclic adduct with 1, 3-dithienium tetrafluoroborate provided compound 56, which has the correct stereochemistry at three key carbons for elaboration to the kempane diterpenes. Exploratory reactions with tricyclic model compounds and with tetracyclic ...