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Synthesis of erythromycin derivatives via the olefin cross-metathesis reaction.
J Org Chem. 2004 May 28; 69(11):3907-11.JO

Abstract

Olefin cross metathesis (CM) was applied to the synthesis of 6-O-substituted erythromycin derivatives. The reactions were catalyzed by transition metal alkylidene complexes, particularly bis(tricyclohexylphosphine)benzylidine ruthenium (IV) dichloride (Grubbs' first-generation catalyst). This approach allowed for the elaboration of the 6-O-allyl group of highly functionalized macrolides at various stages of the synthetic sequence, affording 6-O-3-aryl-propenyl products with excellent E-selectivity. Little or no self-dimerization of the reacting components was found in the crude mixtures. Preliminary kinetic data accounts for the observed cross-selectivity based on substrate reactivity and steric factors.

Authors+Show Affiliations

Hsu MC
Process Chemistry Research and Development, Global Pharmaceutical R&D, Abbott Laboratories, 1401 Sheridan Road, North Chicago, Illinois 60064, USA. margaret.hsu@abbott.com
Junia AJ
No affiliation info available
Haight AR
No affiliation info available
Zhang W
No affiliation info available

MeSH

AlkenesCatalysisErythromycinMolecular StructureOrganometallic CompoundsRutheniumStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

15153024

Citation

Hsu, Margaret C., et al. "Synthesis of Erythromycin Derivatives Via the Olefin Cross-metathesis Reaction." The Journal of Organic Chemistry, vol. 69, no. 11, 2004, pp. 3907-11.
Hsu MC, Junia AJ, Haight AR, et al. Synthesis of erythromycin derivatives via the olefin cross-metathesis reaction. J Org Chem. 2004;69(11):3907-11.
Hsu, M. C., Junia, A. J., Haight, A. R., & Zhang, W. (2004). Synthesis of erythromycin derivatives via the olefin cross-metathesis reaction. The Journal of Organic Chemistry, 69(11), 3907-11.
Hsu MC, et al. Synthesis of Erythromycin Derivatives Via the Olefin Cross-metathesis Reaction. J Org Chem. 2004 May 28;69(11):3907-11. PubMed PMID: 15153024.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of erythromycin derivatives via the olefin cross-metathesis reaction. AU - Hsu,Margaret C, AU - Junia,Adam J, AU - Haight,Anthony R, AU - Zhang,Weijiang, PY - 2004/5/22/pubmed PY - 2004/9/21/medline PY - 2004/5/22/entrez SP - 3907 EP - 11 JF - The Journal of organic chemistry JO - J Org Chem VL - 69 IS - 11 N2 - Olefin cross metathesis (CM) was applied to the synthesis of 6-O-substituted erythromycin derivatives. The reactions were catalyzed by transition metal alkylidene complexes, particularly bis(tricyclohexylphosphine)benzylidine ruthenium (IV) dichloride (Grubbs' first-generation catalyst). This approach allowed for the elaboration of the 6-O-allyl group of highly functionalized macrolides at various stages of the synthetic sequence, affording 6-O-3-aryl-propenyl products with excellent E-selectivity. Little or no self-dimerization of the reacting components was found in the crude mixtures. Preliminary kinetic data accounts for the observed cross-selectivity based on substrate reactivity and steric factors. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/15153024/Synthesis_of_erythromycin_derivatives_via_the_olefin_cross_metathesis_reaction_ DB - PRIME DP - Unbound Medicine ER -