American Chemical Society
ol5b00086_si_001.pdf (8.21 MB)

Total Synthesis of (+)-Vibsanin A

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journal contribution
posted on 2015-02-06, 00:00 authored by Ken-ichi Takao, Kohei Tsunoda, Takuya Kurisu, Akihiro Sakama, Yoshiyasu Nishimura, Keisuke Yoshida, Kin-ichi Tadano
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.