Total synthesis of (+)-vibsanin A

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

doi:10.1021/acs.orglett.5b00086

Total synthesis of (+)-vibsanin A

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

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	756-759
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	3
DOIs	https://doi.org/10.1021/acs.orglett.5b00086
Publication status	Published - 2015 Feb 6

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.5b00086

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AU - Takao, Ken Ichi

AU - Tsunoda, Kohei

AU - Kurisu, Takuya

AU - Sakama, Akihiro

AU - Nishimura, Yoshiyasu

AU - Yoshida, Keisuke

AU - Tadano, Kin Ichi

PY - 2015/2/6

Y1 - 2015/2/6

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AB - 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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Total synthesis of (+)-vibsanin A

Abstract

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