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Synlett 2001; 2001(Special Issue): 1019-1023
DOI: 10.1055/s-2001-14651
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A First Generation Total Synthesis of (+)-Salicylihalamide A

Amos B. Smith III* , Junying Zheng
  • *Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, PA 19104, USA; E-mail: smithab@sas.upenn.edu
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Publikationsdatum:
31. Dezember 2001 (online)

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An efficient total synthesis of (+)-salicylihalamide (1) is described. The synthetic strategy features a highly E-selective ring-closing metathesis to construct the 12-membered salicylihalamide. A macrocycle and a practical method for installation of the labile ene-hepta-(Z,Z)-dienamide side chain, which relies on a Curtius rearrangement to forge the C18-N bond with subsequent N-acylation.

salicylihalamide - total synthesis - macrocycles - metathesis - Curtius rearrangement