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Synlett 1995; 1995(SI): 498-500
DOI: 10.1055/s-1995-5276
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Studies Towards the Total Synthesis of the Marine-Derived Immunosuppressant Discodermolide: Stereoselective Synthesis of a C9-C24 Subunit

Ian Paterson* , Achim Schlapbach
  • *University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK
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Publication History

Publication Date:
31 December 2000 (online)

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Enone 3, an advanced C9-C24 subunit of discodermolide, was synthesised in 17 steps starting from the ethyl ketone (R)-4. The sequence 19 → 23 was developed to introduce the Z-alkene at C13, enabling the conversion of 3 into the complete segment 5.

immunosuppressant - polypropionate - aldol - 1,3-diene - Nozaki-Hiyama reaction