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Synlett 1998; 1998(4): 373-374
DOI: 10.1055/s-1998-1683
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Versatile Synthesis of Bicyclo[9.3.1]pentadecatriene for New Bicyclic Taxoids

Satoshi Shibuya* , Minoru Isobe
  • *Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan; Fax + 81-52-789-4111
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Publication Date:
31 December 2000 (online)

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A common carbon skeleton bicyclo[9.3.1]pentadecatriene of taxachitrienes was synthesized in its des-methyl form in short steps. The key step was Nicholas-Hosomi type reaction in the acidic cyclization between ene-yne biscobalthexacarbonyl complex electrophile with allyltrimethylsilane nucleophile. Decomplexation of the biscobalthexacarbonyl was achieved with a tin hydride and NBS in 1,4-cyclohexadiene solvent.

bicyclo[9.3.1]pentadecatriene - acetylene biscobalthexacarbonyl - Hosomi-Sakurai condition - Nicholas reaction - cation cyclization