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The exact mechanism of the oxidative rearrangement is unknown at this time and alternative mechanisms are certainly possible. An interesting alternative mechanism suggested by a reviewer included a Meisenheimer-type rearrangement of an N-oxide to the O-p-methoxybenzyl hydroxylamine, N-oxidation, and Cope elimination to afford the free hydroxylamine.
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We were also able to reduce 21 to 2 with DIBAL-H; however, the workup and isolation proved more difficult. A similar reduction of both functionalities with DIBAL-H on a fully protected intermediate was employed in a previous total synthesis reported by Danishefsky and co-workers (see reference [9b]).
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A previous report (see reference [9c]) demonstrated the successful oxidation of monoacetylated FR66979 by Swern oxidation.
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After submission of our manuscript, we recently learned that Professor Tohru Fukuyama and co-workers (Tokyo University) and Prof. Marco Ciufolini and co-workers (Université Claude Bernard Lyon 1) have independently completed syntheses of FR900482 and FR66979, respectively. We appreciate receiving preprints of their manuscripts. See the following communications: M. Suzuki, M. Kambe, H. Tokuyama, T. Fukuyama, Angew. Chem. 2002, 114, 4880; Angew. Chem. Int. Ed. 2002, 41, 4686; R. Ducray, M. A. Ciufolini, Angew. Chem. 2002, 114, 4882; Angew. Chem. Int. Ed. 2002, 41, 4688.
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After submission of our manuscript, we recently learned that Professor Tohru Fukuyama and co-workers (Tokyo University) and Prof. Marco Ciufolini and co-workers (Université Claude Bernard Lyon 1) have independently completed syntheses of FR900482 and FR66979, respectively. We appreciate receiving preprints of their manuscripts. See the following communications: M. Suzuki, M. Kambe, H. Tokuyama, T. Fukuyama, Angew. Chem. 2002, 114, 4880; Angew. Chem. Int. Ed. 2002, 41, 4686; R. Ducray, M. A. Ciufolini, Angew. Chem. 2002, 114, 4882; Angew. Chem. Int. Ed. 2002, 41, 4688.
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(2002)
Angew. Chem. Int. Ed.
, vol.41
, pp. 4686
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72
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0001210837
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-
After submission of our manuscript, we recently learned that Professor Tohru Fukuyama and co-workers (Tokyo University) and Prof. Marco Ciufolini and co-workers (Université Claude Bernard Lyon 1) have independently completed syntheses of FR900482 and FR66979, respectively. We appreciate receiving preprints of their manuscripts. See the following communications: M. Suzuki, M. Kambe, H. Tokuyama, T. Fukuyama, Angew. Chem. 2002, 114, 4880; Angew. Chem. Int. Ed. 2002, 41, 4686; R. Ducray, M. A. Ciufolini, Angew. Chem. 2002, 114, 4882; Angew. Chem. Int. Ed. 2002, 41, 4688.
-
(2002)
Angew. Chem.
, vol.114
, pp. 4882
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-
Ducray, R.1
Ciufolini, M.A.2
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73
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0037121441
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After submission of our manuscript, we recently learned that Professor Tohru Fukuyama and co-workers (Tokyo University) and Prof. Marco Ciufolini and co-workers (Université Claude Bernard Lyon 1) have independently completed syntheses of FR900482 and FR66979, respectively. We appreciate receiving preprints of their manuscripts. See the following communications: M. Suzuki, M. Kambe, H. Tokuyama, T. Fukuyama, Angew. Chem. 2002, 114, 4880; Angew. Chem. Int. Ed. 2002, 41, 4686; R. Ducray, M. A. Ciufolini, Angew. Chem. 2002, 114, 4882; Angew. Chem. Int. Ed. 2002, 41, 4688.
-
(2002)
Angew. Chem. Int. Ed.
, vol.41
, pp. 4688
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-
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