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Published on: May 31, 2024
Total synthesis of (+)-vibsanin A
Ken-ichi Takao1, Kohei Tsunoda, Takuya Kurisu
1Department of Applied Chemistry, Keio University , Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
Abstract:
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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