Convergent synthesis of pyragonicin |
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Authors: | Takahashi Shunya Hongo Yayoi Ogawa Narihito Koshino Hiroyuki Nakata Tadashi |
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Institution: | RIKEN (The Institute of Physical and Chemical Research), Wako-shi, Saitama, 351-0198, Japan. shunyat@riken.go.jp |
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Abstract: | This paper describes a second-generation synthesis of an antitumor tetrahydropyran (THP) acetogenin, pyragonicin. The key step involved an olefin cross-metathesis between the THP segment and the terminal gamma-lactone residue. The coupling reaction in the presence of Grubbs' second-generation catalyst resulted in an unseparable mixture of a desired coupling product and its one-carbon eliminated product while the use of Grubbs' first-generation catalyst afforded the former exclusively. A novel MOM-migrating reaction found in a cyclization reaction is also discussed. |
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