Total synthesis of (+)-vibsanin A

Ken Ichi Takao, Kohei Tsunoda, Takuya Kurisu, Akihiro Sakama, Yoshiyasu Nishimura, Keisuke Yoshida, Kin Ichi Tadano

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)756-759
Number of pages4
JournalOrganic Letters
Volume17
Issue number3
DOIs
Publication statusPublished - 2015 Feb 6

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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