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Synlett 2001; 2001(3): 0365-0368
DOI: 10.1055/s-2001-11403
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Synthesis of the Oxygenated Bicyclo[9.3.1]pentadecane Ring System of Phomactin A using Chromium (II)-mediated Macrocyclisation and Ring Closure Metathesis

Kevin M. Foote* , Matthew John, Gerald Pattenden
  • *School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK; E-mail: gp@nottingham.ac.uk
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Publication Date:
31 December 2001 (online)

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Treatment of the aldehyde vinyl iodides 17, 19 a and 19 b in DMSO with CrCl2-NiCl2 resulted in their macrocyclisation to the oxygenated ring systems 18, 20, and 21 respectively (43-63%) of the PAF antagonist phomactin A isolated from the marine fungus Phoma sp. The same bicyclo[9.3.1]pentadecane ring system 24 could also be produced by treatment of the polyene 23 with Grubbs' ruthenium catalyst in hot CH2Cl2 for 10 h (∼ 30%).

macrocyclisation - chromium (II) - phomactin A - metathesis - PAF