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Synthesis 1995; 1995(2): 195-198
DOI: 10.1055/s-1995-3871
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Synthesis of the C16-C23 Effector Domain of FK-506 via Copper-Catalysed Metallate Rearrangement of an α-Alkoxyalkenylcuprate

Krzysztof Jarowicki, Philip Kocienski* , Simon Norris, Michael O’Shea, Michael Stocks
  • *Department of Chemistry, The University, Southampton, SO17 1BJ, U.K.
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Publication Date:
31 December 2000 (online)

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A 1,2-metallate rearrangement of the putative higher order cuprate 17 derived from reaction of the metallated dihydrofuran 15 with the homocuprate 16 occurred with clean inversion of configuration to give the alkenylcuprate 18. Methylation of 18 followed by five simple transformations completed the synthesis of the C16-C23 effector domain of the immunosuppressant FK-506.

immunosuppressant - FK-506 - effector domain - 1,2-metallate rearrangement - higher order cuprate