The marine natural product 16-deacetoxy-12-epi-scalarafuranacetate, isolated from Spongua officinalis , was synthesized in 18 linear steps, starting from (-)-sclareol, with high stereoselectivity and an overall yield of 6.1%. The intermediate 16-deacetoxy-12-epi-scalarafuran could be easily transformed into a series of natural scalarane sesterterpenoids in a few steps.

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An efficient procedure is described for the oxidative homocoupling of functionalized Grignard reagents using a catalytic amount of dilithium tetrachlorocuprate(II) (CuLi 2 Cl 4) in the presence of pure oxygen gas. This method is applied successfully to a variety of aryl, heteroaryl, alkyl, alkenyl and alkynyl halides, which are converted into the corresponding homocoupled products in good to excellent yields.

Dilithium Tetrachlorocuprate(II) Catalyzed Oxidative Homocoupling of Functionalized Grignard Reagents. -A practical method is demonstrated, which is applicable to alkyl, alkynyl, and aromatic magnesium halides. -(HUA, S.-K.; HU, Q.-P.; REN, J.; ZENG*, B.-B.; Synthesis 45 (2013) 4, 518-526, http://dx.