Synthesis of `Molecular Asterisks' via Sequential Cross-Metathesis, Sonogashira and Cyclotrimerization Reactions

Romyr Dominique; Bingcan Liu; Sanjoy K. Das; René Roy

doi:10.1055/s-2000-6266

Synthesis 2000; 2000(6): 862-868
DOI: 10.1055/s-2000-6266

special topic

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Synthesis of `Molecular Asterisks' via Sequential Cross-Metathesis, Sonogashira and Cyclotrimerization Reactions

Romyr Dominique^* , Bingcan Liu, Sanjoy K. Das, René Roy

^*Department of Chemistry, University of Ottawa, Ontario, Canada K1N 6N5; Fax +1 (6 13) 5 62 51 70; E-mail: rroy@science.uottawa.ca

Abstract

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A series of suitably functionalized C-linked carbohydrate derivatives 9-13 were prepared in good yields from alkenyl glycosides 1-4 by cross-metathesis reaction using Grubbs' catalyst [Cl₂(PCy₃)₂Ru=CHPh]. The reaction was also applied to 6-O-allyl ether 5 and N-Cbz allylamine 6. C-Linked glycopeptide homologue 15 was prepared in 65% yield by cross-metathesis of perbenzylated β-C-allyl mannopyranoside 1 and allyl glycine derivative 8. Finally, amine-ending C-glycoside 11 was subjected to a sequence of deprotection, amidation with p-iodobenzoic acid (EDC, HOBt, DIPEA, r.t., 12 h), Sonogashira reaction [Pd(PPh₃)₂Cl₂, Et₃N, 65 °C, 6 h] and treatment with dicobalt octacarbonyl (60 °C, 6 h) to provide a `molecular asterisk' 21 in 53% yield.

cross-metathesis - carbohydrates - glycopeptides - Sonogashira reaction - cyclotrimerization - ruthenium

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