Studies on Taxane Synthesis III.Stereocontrolled Synthesis of a Twelve-Membered Lactam Sulfide as a Precursor of 4,8,11,11-Tetramethyl-3-oxobicyclo[5.3.1]undec-8-ene

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概要

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• Stereocontrolled synthesis of two twelve-membered lactam sulfides 37 and 38 as precurors of 8,11,11-trimethyl-3-oxobicyclo[5.3.1]undec-8-enes constituting the A and B rins of taxane-diterpenes was achieved.The keystep involves a Diels-Alder reaction of maleic anhydride and the E-diene 18 for introduction of the requisite cis arrangement of substitutions at the C-1 and C-7 positions.The resulting adduct was converted exclusively into the lactone 21b in five steps : 1) hydrolysis, 2) iodo-lactonization, 3) BH_3 reduction, 4) Zn reduction, 5) methylation.The benzyl group of 26 could be selectively removed by heating with Raney Ni(W-2) in EtOH in nearly quantitative yield without hydrogenation of the double bond.

• 公益社団法人日本薬学会の論文
• 1991-06-25

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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