The first total synthesis of (+)-vibsanin A, an 11-membered vibsane diterpenoid, was achieved, unambiguously establishing its relative and absolute stereochemistry. Highlights of the synthesis include the stereoselective formation of an all-carbon quaternary stereocenter by a zinc-mediated Barbier-type allylation in an aqueous medium, and the efficient construction of an 11-membered ring skeleton by a combination of an intramolecular Nozaki-Hiyama-Kishi (NHK) reaction and a Mitsunobu reaction.

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Construction of All-Carbon Quaternary Stereocenters by Zinc-Mediated Barbier-Type Allylation in AqueousMedia. -(TAKAO*, K.-I.; MIYASHITA, T.; AKIYAMA, N.; KURISU, T.; TSUNODA, K.; TADANO, K.-I.; Heterocycles 86 (2012) 1, 147-153, http://dx.doi.org/10.3987/com-12-s(n)31 ; Dep. Appl. Chem., Fac. Sci. Technol., Keio Univ., Kohoku, Yokohama 223, Japan; Eng.) -R. Staver

Total Synthesis of (+)-Vibsanin A. -(TAKAO*, K.-I.; TSUNODA, K.; KURISU, T.; SAKAMA, A.; NISHIMURA, Y.; YOSHIDA, K.; TADANO, K.-I.; Org. Lett. 17 (2015) 3, 756-759, http://dx.doi.org/10.1021/acs.orglett.5b00086 ; Dep. Appl. Chem., Fac. Sci. Technol., Keio Univ., Kohoku, Yokohama 223, Japan; Eng.) -Mais 26-254