Synthetic studies of pestalotiopsin A: asymmetric synthesis of the 2-oxabicyclo[3.2.0]heptane substructure |
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Authors: | Ken-ichi Takao |
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Institution: | Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan |
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Abstract: | A functionalized 2-oxabicyclo3.2.0]heptan-3-one derivative, possessing all the skeletal carbons of pestalotiopsin A, has been synthesized. For the preparation of intermediary cyclobutane derivatives in enantioenriched form, the Lewis acid-catalyzed 2+2] cycloaddition of N-propiolated Oppolzer’s camphorsultam with dimethylketene bis(trimethylsilyl) acetal followed by a stereoselective 1,4-hydride addition/protonation, has been developed. |
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Keywords: | Cyclobutane [2+2] Cycloaddition Chiral auxiliary |
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