Studies on Taxane Synthesis. II. : Synthese of 3,8,11,11-Tetramethyl-4-oxo- and 4,8,11,11-Tetramethyl-3-oxo-bicyclo[5.3.1]undec-8-enes Corresponding to the A- and B-Rings of Taxane Diterpenes

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概要

• 論文の詳細を見る

• Two types of tetramethylbicyclo[5.3.1]undec-8-enes 2 and 3 were synthesize from α-ionone as a model for taxane synthesis. Introduction of the requisite cis-arrangement of substitutents as the C-1 and C-7 positions was carried out by catalytic hydrogenation of the α, β-unsaturated ketone 12. Treatment of the hydroxy estaer 27 and 16 with diethyl azodicarboxylate and triphenylphosphine led to regioselective dehydration giving 33 and 43,respectively. Intramolecular cyclization of 41 and 49 with lithium diisopropylamide followed by reductive desulfurization with Na-Hg produced the eight-membered ring ketones 2 and 3,respectively, in good yields.

• 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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