Total Synthesis of (+)-Cytosporolide A via a Biomimetic Hetero-Diels-Alder Reaction

Kenichi Takao, Shuji Noguchi, Shu Sakamoto, Mizuki Kimura, Keisuke Yoshida, Kin Ichi Tadano

研究成果: Article査読

28 被引用数 (Scopus)

抄録

The first total synthesis of (+)-cytosporolide A was achieved by a biomimetic hetero-Diels-Alder reaction of (¯)-fuscoatrol A with o-quinone methide generated from (+)-CJ-12,373. The dienophile, highly oxygenated caryophyllene sesquiterpenoid (¯)-fuscoatrol A, was synthesized from the synthetic intermediate in our previous total synthesis of (+)-pestalotiopsin A. The o-quinone methide precursor, isochroman carboxylic acid (+)-CJ-12,373, was synthesized through a Kolbe-Schmitt reaction and an oxa-Pictet-Spengler reaction. The hetero-Diels-Alder reaction of these two compounds proceeded with complete chemo-, regio-, and stereoselectivity to produce the complicated pentacyclic ring system of the cytosporolide skeleton. This total synthesis unambiguously demonstrates that natural cytosporolide A has the structure previously suggested.

本文言語English
ページ(範囲)15971-15977
ページ数7
ジャーナルJournal of the American Chemical Society
137
50
DOI
出版ステータスPublished - 2015 12 23

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

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