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Synlett 2000; 2000(8): 1123-1126
DOI: 10.1055/s-2000-6750
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Use of Malonate Connectors in Solid Phase Organic Chemistry. Application to the Synthesis of Macrocarbocycles

Pierre Soucy* , Yves L. Dory, Pierre Deslongchamps
  • *Laboratoire de Synthèse Organique, Département de Chimie, Institut de Pharmacologie de Sherbrooke, Université de Sherbrooke, 3001, 12e avenue nord, Sherbrooke (Québec), Canada J1H 5N4; Fax (819) 820 68 23; E-mail: yves.dory@courrier.usherb.ca
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Publication Date:
31 December 2000 (online)

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The malonate unit is linked to solid supports and multistep syntheses of macrocycles are then carried out. Various reactions are studied on solid supports and this investigation finally reveals that Solid Phase Organic Chemistry (SPOC) is a reliable technology even for long sequences. The cyclizations using malonate anion SN2 on allylic chlorides lead mostly to polymers and indicate that pseudo-high dilution conditions are not found on solid support.

multi-step solid phase synthesis - macrocycles - malonates - ring closure - high dilution