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Volumn 41, Issue 24, 2002, Pages 4683-4685

Concise enantioselective synthesis of (+)-FR66979 and (+)-FR900482: Dimethyldioxirane-mediated construction of the hydroxylamine hemiketal

Author keywords

Antitumor agents; Asymmetric synthesis; Hydroxylamines; Natural products; Total synthesis

Indexed keywords

ANTIBIOTICS; HYDROGEN BONDS; OXIDATION; SYNTHESIS (CHEMICAL); TUMORS;

EID: 0037122113     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200290015     Document Type: Article
Times cited : (63)

References (73)
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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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    • note
    • 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.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4686
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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
    • Ducray, R.1    Ciufolini, M.A.2
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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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