Total synthesis of the proposed structure for pyragonicin |
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Authors: | Takahashi Shunya Ogawa Narihito Koshino Hiroyuki Nakata Tadashi |
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Institution: | RIKEN (The Institute of Physical and Chemical Research), Wako, Saitama 351-0198, Japan. shunyat@postman.riken.go.jp |
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Abstract: | structure: see text] The total synthesis of acetogenin 1 reported for pyragonicin and its 10-epimer 32 is described. The common THP ring system was stereoselectively constructed through a SmI(2)-induced reductive cyclization of beta-alkoxy acrylate 5 followed by Mitsunobu inversion, and each chiral center at C-10 was created by Brown's asymmetric allylation. Compound 1 had spectroscopic data consistent with that of natural pyragonicin, but a different optical rotation. |
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