An Olefin Metathesis Approach to 36- And 72-Membered Archaeal Macrocyclic Membrane Lipids

Journal of Organic Chemistry

Volumn 63, Issue 14, 1998, Pages 4741-4745

  Arakawa, Kenji ^a   Eguchi, Tadashi ^a   Kakinuma, Katsumi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001311256     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980472k     Document Type: Article

References (46)

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2. For reviews: see (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (b) Grubbs, R. H. Alkene Metathesis and Related Reactions; Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol 5, p 1115.
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43. Methylene chloride was the most effective solvent for the metathesis reaction of 5 and was used throughout the present study.
44. In our preliminary experiments using desmethylated model compound i, the RCM reaction occurred more rapidly than for 5. The acyclic diene i was converted to ii under high dilution conditions (substrate concentration, 2.9 mM). Equation presented.
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46. The ring-opening metathesis in the case of the compound ii proceeded in 12% yield to afford iii, together with the recovered ii (88%). The different reactivities of ii and 6 are probably due to a steric factor. Equation presented.