Studies on Taxane Synthesis. I. : Synthesis of 3,8,11,11-Tetramethyl-4-oxobicyclo[5.3.1]undecane as a Model for Taxane Synthesis

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概要

• 論文の詳細を見る

• The bicyclo[5.3.1]undecanone 5 corresponding to the A and B rings in taxane diterpenes was synthesize from β-ionone. Reduction of the tosylhydrazone 11 with catecholborane afforded the trisubstituted olefin 12 having trans substitutents at the C-1 and C-7 positions. The requisite cisarrangement of these substituents for eight-membered ring formation was induced by epimerization of the aldehyde 13 to give the bicyclic hemiacetal 14. The lithium diissopropylamide-promoted intramolecular cyclization of the twelve-membered lactam sufoxide 32 proceeded quite smoothy, affording the eight-membered keto sulfoxide 33 in quantitative yield.

• 公益社団法人日本薬学会の論文
• 1988-12-25

著者

• 大石 武

  Riken Institute (The Institute of Physical and Chemical Research)

• 大石 武

  Faculty Of Engineering Yokohama National University:(present Address)meiji College Of Pharmacy

• 大石 武

  理研:(現)明治薬科大学

• 大塚 晏央

  Faculty Of Engineering Yokohama National University:(present Address)pharmaceutical Research Center

• 大塚 晏央

  RIKEN (The Institute of Physical and Chemical Research)

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