Total synthesis of a new cytotoxic acetogenin, jimenezin, and the revised structure |
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Authors: | Takahashi S Maeda K Hirota S Nakata T |
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Institution: | RIKEN (The Institute of Physical and Chemical Research), Saitama, Japan. shunyat@riken.go.jp |
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Abstract: | The first total synthesis of jimenezin was achieved by using carbohydrates as chiral building blocks, thus revising the proposed structure 1 to 2. The key steps in this synthesis include an efficient construction of the THP-THF fragments 3 and 16 through a stereoselective condensation between the pyranyl aldehyde 5 and the acetylene derivative 6, and a palladium-catalyzed coupling reaction of 3 or 16 with a terminal butenolide 4. |
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