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During our study, very recently the Sasaki and Tachibana group reported the first total synthesis of 1. (a) Fuwa, H.; Sasaki, M.; Satake, M.; Tachibana, K. Org. Lett. 2002, 4, 2981-2984.
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0012371397
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note
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For the preparation of 3 and 4, see Supporting Information.
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0012456444
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note
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N2 pathway. The D ring of the desired isomer 2, in which all of the substituents take an equatorial position, is more thermally stable than that of 9. The details of the mechanism are under investigation. We appreciate a referee who pointed out the above problems, and we also thank Professor T. Oishi (Osaka University) and Professor M. Inoue (Tohoku University) for suggesting the use of the chloroacetyl group.
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0012374134
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note
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For the determination of the stereochemistries of 2 and 9, see Supporting Information.
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0012471867
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note
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Fuji Silysia silica gel was used for the purification of 1. Although the detail is not clear, the use of Kanto Chemical silica gel (neutral) caused partial isomerization of 1. See Supporting Information.
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