Total synthesis of FK506 and an FKBP probe reagent,[C (8), C (9)-13C2]-FK506

M Nakatsuka, JA Ragan, T Sammakia…

Index: Nakatsuka, Masashi; Ragan, John A.; Sammakia, Tarek; Smith, David B.; Uehling, David E.; Schreiber, Stuart L. Journal of the American Chemical Society, 1990 , vol. 112, # 14 p. 5583 - 5601

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Citation Number: 246

Abstract

Abstract: Asymmetric syntheses of FK506 and (C8, C9-L3C2)-FK506 are reported. The latter compound was designed to facilitate an investigation of the interactions between FK506 and its receptor, the recently discovered immunophilin, FKBP. The syntheses involved the preparation of intermediates 7-9 in nonracemic form; the key coupling reactions included a Cram-selective addition of the vinyl Grignard reagent derived from bromide 9 to aldehyde ...

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