Acid-catalyzed Rearrangement of Epoxy Alcohol Derivatives Having the Electron-withdrawing Protective Groups (Acyl or Sulfonyl): Asymmetric Synthesis of Chiral Quaternary Carbon and Spiro Centers and Its Application to Natural Products Synthesis.

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  • 電子求引性保護基（アシル基，スルホニル基）を持つエポキシアルコール類の酸転位反応　　不斉四級炭素および不斉スピロ中心の構築と天然物合成への応用
  • デンシキュウインセイ ホゴキ アシルキ スルホニルキ オ モツ エポキシアルコールルイ ノ サン テンイ ハンノウ フセイ 4キュウ タンソ オヨビ フセイ スピロ チュウシン ノ コウチク ト テンネンブツ ゴウセイ エ ノ オウヨウ

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Rearrangements of 1, 2-epoxy alcohol derivatives having electron-withdrawing protective groups such as acyl or sulfonyl group have been developed leading to the asymmetric construction of chiral quaternary carbon centers and spiro centers. The success of the novel rearrangements here depends on the electron-withdrawing property of the protective groups. The methods were applied to the asymmetric syntheses of several natural products such as fredericamycin A, (+) - (S) -sporochnol A, (-) -aphanorphine, and (-) -a-herbertenol.

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