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Several numbering schemes are in use for rapamycin. We have opted to maintain the scheme previously employed by us (L.W.R.; D.A.H.) and originated by the group responsible for the structure elucidation of rapamycin. Findlay, J. A.; Radics, L. Can. J. Chem. 1980, 58, 579-590.
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4 similarly and more rapidly yields its oxepane tautomer which reverts to pyran during chromatography (Wu Yang, unpublished). Hughes has reported the preparation and isolation of the oxepane tautomer of rapamycin: Hughes, P.; Musser, J.; Conklin, M.; Russo, R. Tetrahedron Lett. 1992, 33, 4739-4742. (Matrix Presented)
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4 has been utilized in macrolide total synthesis to facilitate ring size equilibration through transesterification; Kigoshi, H.; Suenaga, K.; Mutou, T.; Ishigaki, T.; Atsumi, T.; Ishiwata, H.; Sakakura, A.; Ogawa, T.; Ojika, M.; Yamada, K. J. Org. Chem. 1996, 61, 5326-5351, Paterson, I.; Watson, C.; Yeung, K.-S.; Wallace, P. A.; Ward, R. A. J. Org. Chem. 1997, 62, 452-453.
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4 has been utilized in macrolide total synthesis to facilitate ring size equilibration through transesterification; Kigoshi, H.; Suenaga, K.; Mutou, T.; Ishigaki, T.; Atsumi, T.; Ishiwata, H.; Sakakura, A.; Ogawa, T.; Ojika, M.; Yamada, K. J. Org. Chem. 1996, 61, 5326-5351, Paterson, I.; Watson, C.; Yeung, K.-S.; Wallace, P. A.; Ward, R. A. J. Org. Chem. 1997, 62, 452-453.
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