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

• 大塚 晏央

  RIKEN (The Institute of Physical and Chemical Research)

• 大石 武

  RIKEN (The Institute of Physical and Chemical Reserch)

抄録

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.

収録刊行物

• Chemical & pharmaceutical bulletin

  Chemical & pharmaceutical bulletin 39 (6), 1359-1364, 1991-06-25

  公益社団法人日本薬学会

キーワード

• taxane-type diterpene
• stereocontrolled synthesis
• Diels-Alder reaction
• iodo-lactonization
• anhydride
• NaBH_4 reduction
• BH_3 reduction
• Raney Ni
• selective debenzylation
• twelve-membered lactan sulfide

詳細情報

• CRID: 1571698602415076608
• NII論文ID: 110003629344
• NII書誌ID: AA00602100
• ISSN: 00092363
• 本文言語コード: en
• データソース種別:
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