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Total Synthesis of (+)-Vibsanin A
Organic Letters ( IF 4.9 ) Pub Date : 2015-01-26 00:00:00 , DOI: 10.1021/acs.orglett.5b00086
Ken-ichi Takao 1 , Kohei Tsunoda 1 , Takuya Kurisu 1 , Akihiro Sakama 1 , Yoshiyasu Nishimura 1 , Keisuke Yoshida 1 , Kin-ichi Tadano 1
Affiliation  

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.

中文翻译:

(+)-Vibsanin A的全合成

实现了第一个全合成的(+)-vibsanin A(一种11元的visane二萜类化合物),明确地建立了其相对和绝对立体化学。合成的亮点包括在水介质中通过锌介导的Barbier型烯丙基化立体选择性地形成全碳四级立体中心,以及结合分子内的Nozaki–Hiyama–高效构建11元环骨架Kishi(NHK)反应和Mitsunobu反应。
更新日期:2015-01-26
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